cas 592-31-4, N-Butylurea | Articles data

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Green and efficient synthesis of thioureas, ureas, primary: O -thiocarbamates, and carbamates in deep eutectic solvent/catalyst systems using thiourea and urea
An efficient and general catalysis process was developed for the direct preparation of various primary O-thiocarbamates/carbamates as well as monosubstituted thioureas/ureas by using thiourea/urea as biocompatible thiocarbonyl (carbonyl) sources. This procedure used choline chloride/tin(ii) chloride [ChCl][SnCl2]2 with a dual role as a green catalyst and reaction medium to afford the desired products in moderate to excellent yields. Moreover, the DES can be easily recovered and reused for seven cycles with no significant loss in its activity. Besides, the method shows very good performance for synthesizing the desired products on a large scale.
Bagherzadeh, Nastaran,Sardarian, Ali Reza,Inaloo, Iman Dindarloo
supporting information
p. 11852 - 11858
(2021/07/12)

A Straightforward Synthesis of N-Substituted Ureas from Primary Amides
A direct and convenient method for the preparation of N-substituted ureas is achieved by treating primary amides with phenyliodine diacetate (PIDA) in the presence of an ammonia source (NH 3 or ammonium carbamate) in MeOH. The use of 2,2,2-trifluoroethanol (TFE) as the solvent increases the electrophilicity of the hypervalent iodine species and allows the synthesis of electron-poor carboxamides. This transformation involves a nucleophilic addition of ammonia on the isocyanate intermediate generated in situ by a Hofmann rearrangement of the starting amide.
Franck, Xavier,Glachet, Thomas,Ibert, Quentin,Lohier, Jean-Fran?ois,Reboul, Vincent,Saraiva Rosa, Nathalie
p. 2099 - 2105
(2020/07/13)

An efficient one-pot synthesis of industrially valuable primary organic carbamates and: N -substituted ureas by a reusable Merrifield anchored iron(ii)-anthra catalyst [FeII(Anthra-Merf)] using urea as a sustainable carbonylation source
An efficient synthesis of primary carbamates and N-substituted ureas is explored with a newly developed heterogeneous polymer supported iron catalyst in the presence of a sustainable carbonylation source. The Merrifield anchored iron(ii)-anthra catalyst [FeII(Anthra-Merf)] was synthesized by functionalization of Merrifield polymer followed by grafting of iron metal. The catalyst [FeII(Anthra-Merf)] was characterized by several techniques, like SEM, EDAX, TGA, PXRD, XPS, FTIR, CHN, AAS and UV-Vis analysis. The designed polymer embedded [FeII(Anthra-Merf)] complex is a remarkably successful catalyst for the synthesis of primary organic carbamates and N-substituted ureas by using safe carbonylation agent urea with different derivatives of alcohols and amines, respectively. The reported catalyst is a potential candidate towards contributing a satisfactory yield of isolated products under suitable reaction conditions. The catalyst is recyclable and almost non-leaching in nature after six runs with an insignificant drop in catalytic activity. Thus we found an economical and viable catalyst [FeII(Anthra-Merf)] for primary carbamates and N-substituted urea synthesis under moderate reaction conditions.
Basu, Priyanka,Dey, Tusar Kanto,Ghosh, Aniruddha,Biswas, Surajit,Khan, Aslam,Islam, Sk. Manirul
p. 2630 - 2643
(2020/02/20)

A practically simple, catalyst free and scalable synthesis of: N -substituted ureas in water
A practically simple, mild and efficient method is developed for the synthesis of N-substituted ureas by nucleophilic addition of amines to potassium isocyanate in water without organic co-solvent. Using this methodology, a variety of N-substituted ureas (mono-, di- and cyclic-) were synthesized in good to excellent yields with high chemical purity by applying simple filtration or routine extraction procedures avoiding silica gel purification. The developed methodology was also found to be suitable for gram scale synthesis of molecules having commercial application in large volumes. The identified reaction conditions were found to promote a unique substrate selectivity from a mixture of two amines.
Tiwari, Lata,Kumar, Varun,Kumar, Bhuvesh,Mahajan, Dinesh
p. 21585 - 21595
(2018/06/26)

Superparamagnetic Fe3O4 Nanoparticles in a Deep Eutectic Solvent: An Efficient and Recyclable Catalytic System for the Synthesis of Primary Carbamates and Monosubstituted Ureas
Superparamagnetic Fe3O4 nanoparticles were used to synthesize various primary carbamates as well as monosubstituted and N,N-disubstituted ureas. This efficient phosgene-free process used urea as an eco-friendly carbonyl source in the presence of a biocompatible deep eutectic solvent (DES) to provide an inexpensive and attractive route that afforded the products in moderate to excellent yields. The employed DES serves both a catalytic role and as the green reaction medium. The magnetic nanocatalyst and DES can been reused several times without a significant loss of activity.
Inaloo, Iman Dindarloo,Majnooni, Sahar,Esmaeilpour, Mohsen
p. 3481 - 3488
(2018/07/29)

XANTHINE DERIVATIVE INHIBITORS OF BET PROTEINS
This invention relates to xanthine derivative compounds that are inhibitors of BET bromodomains proteins, the method of preparation thereof and applications thereof.
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Page/Page column 93

(2017/07/14)

Exploring Selective Inhibition of the First Bromodomain of the Human Bromodomain and Extra-terminal Domain (BET) Proteins
A midthroughput screening follow-up program targeting the first bromodomain of the human BRD4 protein, BRD4(BD1), identified an acetylated-mimic xanthine derivative inhibitor. This compound binds with an affinity in the low micromolar range yet exerts suitable unexpected selectivity in vitro against the other members of the bromodomain and extra-terminal domain (BET) family. A structure-based program pinpointed a role of the ZA loop, paving the way for the development of potent and selective BET-BRDi probes.
Raux, Brigitt,Voitovich, Yuliia,Derviaux, Carine,Lugari, Adrien,Rebuffet, Etienne,Milhas, Sabine,Priet, Stéphane,Roux, Thomas,Trinquet, Eric,Guillemot, Jean-Claude,Knapp, Stefan,Brunel, Jean-Michel,Fedorov, Alexey Yu.,Collette, Yves,Roche, Philippe,Betzi, Stéphane,Combes, Sébastien,Morelli, Xavier
supporting information
p. 1634 - 1641
(2016/03/05)

4-Dodecylbenzenesulfonic acid (DBSA) promoted solvent-free diversity-oriented synthesis of primary carbamates, S-thiocarbamates and ureas
A simple and highly efficient solvent-free method for the conversion of alcohols, phenols, thiols and amines to primary carbamates, S-thiocarbamates and ureas in the presence of 4-dodecylbenzenesulfonic acid (DBSA) as a cheap and green Bronsted acid reagent has been described. All products were obtained in good to excellent yields and characterized using FT-IR, 1H- and 13C-NMR, MS and CHNS techniques.
Sardarian, Ali Reza,Inaloo, Iman Dindarloo
p. 76626 - 76641
(2015/09/22)

Carboxylic acid-catalyzed one-pot synthesis of cyanoacetylureas and their cyclization to 6-aminouracils in guanidine ionic liquid
A novel, one-pot, carboxylic acid-catalyzed synthesis of cyanoacetylureas via in situ generated ureas and their cyclization to 6-aminouracils in the presence of the guanidine-based ionic liquid 1,1,3,3-tetramethylguanidine lactate [TMG][Lac] is described. The ureas were synthesized from amines and potassium cyanate, which on reaction with cyanoacetic acid in the presence of acetic anhydride in the same pot afforded cyanoacetylureas, which undergo cyclization in [TMG][Lac] as solvent as well as catalyst to afford 6-aminouracils. One-pot synthesis of cyanoacetylureas, efficient and rapid cyclization, better yield, shorter reaction time, easy workup procedure, and recyclability of the ionic liquid are some advantages of this procedure.
Chavan, Sunil S.,Shelke, Rupesh U.,Degani, Mariam S.
p. 399 - 403
(2013/05/21)

An improved method for the preparation of alkyl/arylurea derivatives using chlorocarbonylsulfenyl chloride as carbonylating agent
A convenient procedure has been developed for preparation of aminesubstituted or monomethylamine-substituted alkyl/arylurea derivatives. The method comprises two steps-reaction of an alkyl/aryl amine with chlorocarbonylsulfenyl chloride in a non-polar solvent to produce an alkyl/arylcarbonylsulfenyl chloride, then reaction of this alkyl/ arylcarbonylsulfenyl chloride with ammonia or monomethylamine in a two-phase reaction with a phase-transfer catalyst, to produce the corresponding alkyl/aryl-substituted urea. Springer Science+Business Media B.V. 2012.
Manidhar,K. Uma Maheswara Rao,C. Suresh Reddy,Ch. Syamasunder,Adeppa,Misra, Krishna
p. 2479 - 2489
(2013/03/13)

Ionic liquid mediated one-pot synthesis of 6-aminouracils
A novel, one-pot synthesis of 6-aminouracils via in situ generated ureas and cyanoacetylureas in the presence of an ionic liquid catalyst, 1,1,3,3-tetramethylguanidine acetate, is described. The catalyst can be recycled for five consecutive runs without loss of activity. The mechanism for the ring closure of cyanoacetylurea to 6-aminouracil is also discussed.
Chavan, Sunil S.,Degani, Mariam S.
supporting information; experimental part
p. 296 - 299
(2012/03/26)

PROCESS FOR STRAIGHTENING KERATIN FIBRES WITH A HEATING MEANS AND DENATURING AGENTS
The invention relates to a process for straightening keratin fibres, comprising: (i) a step in which a straightening composition containing at least two denaturing agents is applied to the keratin fibres, (ii) a step in which the temperature of the keratin fibres is raised, using a heating means, to a temperature of between 110 and 250° C.
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(2010/03/02)

Preparation of mono-, di-, and trisubstituted ureas by carbonylation of aliphatic amines with S,S-dimethyl dithiocarbonate
General procedures are reported to prepare N-alkylureas, N,N′-dialkylureas (both symmetrical and unsymmetrical), and N,N,N′-trialkylureas by carbonylation of aliphatic amines, employing S,S-dimethyl dithiocarbonate (DMDTC) as a phosgene substitute. All reactions were carried out in water. Symmetrical disubstituted ureas were prepared directly working at 60°C with a molar ratio of DMDTC:amine = 1:2, preferably under nitrogen. Unsymmetrical ureas were prepared in two steps via S-methyl N-alkyl-thiocarbamate intermediates, which are formed selectively in the first step at room temperature. These intermediates react in the second step with ammonia or various aliphatic amines, both primary and secondary, at temperatures varying between 50 and 70°C. All the target ureas were obtained in high yields (28 examples, average yield 94%) and with very high purity (generally >99.2%). Also to be noted is the recovery of a co-product of industrial interest, methanethiol, in an amount of two moles for each mole of DMDTC, with complete exploitation of the reagent. Georg Thieme Verlag Stuttgart.
Artuso, Emma,Degani, Iacopo,Fochi, Rita,Magistris, Claudio
p. 3497 - 3506
(2008/09/19)

Process to prepare alkyl-ureas from O,S-dimethyl dithiocarbonate
The present invention relates to the preparation of alkyl-ureas, starting from O,S-dimethyl dithiocarbonate, which provides the following steps: A) causing the O,S-dimethyl dithiocarbonate to react with a primary amine of general formula R1NH2in order to obtain an O-methyl thiocarbamate; B) isomerising the O-methyl thiocarbamate in order to obtain an S-methyl thiocarbamate; C) causing the S-methyl thiocarbamate with a compound of general formula R′R″NH, wherein R′ and R″ may be equal or different one in respect of the other and of R1and may be H, R2or R3, in order to obtain one of the alkyl-ureas of formula (4), (5) or (6).
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(2010/02/06)

Antitumoral compounds
New spisulosine derivatives of use in treating tumors are of the formula (I) wherein: each X is the same or different, and represents H, OH, OR′, SH, SR′, SOR′, SO2R′, NO2, NH2, NHR′, N(R′)2, CN, halogen, C(=O)H, C(=O)CH3, CO2H, CO2CH3, substituted or unsubstituted C1-C18 alkyl, substituted or unsubstituted C2-C18 alkenyl, substituted or unsubstituted C2-C18 alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaromatic, or two groups X may together form =O; Y is NR1, OR1, PR1, SR1, or halogen, wherein the number of substituents R1 is selected to suit the valency and each R1 is independently selected of H, OH, C(=O)R′, P(=O)R′R″, substituted or unsubstituted C1-C18 alkyl, substituted or unsubstituted C2-C18 alkenyl, substituted or unsubstituted C2-C18 alkynyl, substituted or unsubstituted aryl, and wherein the dotted line indicates an optional double bond; each Z is the same different, and represents H, OH, OR′, SH, SR′, SOR′, SO2R′, NO2, NH2, NHR′, N(R′)2, NHC(O)R′, CN, halogen, C(=O)H, C(=O)CH3, CO2H, CO2CH3, substituted or unsubstituted C1-C18 alkyl, substituted or unsubstituted C2-C18 alkenyl, substituted or unsubstituted C2-C18 alkenyl, substituted or unsubstituted C2-C18 alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaromatic, or two groups Z may together form =O; z is 0 to 25; y is to 0 to 20; R2 is H, C(=O)R′, P(=O)R′R″, S(=O)R′R″, S(=O)2R′, substituted or unsubstituted C1-C18 alkyl, substituted or unsubstituted C2-C18 Alkenyl, substituted or unsubstituted C2-C18 alkynyl, substituted or unsubstituted aryl; R3 is H, C(=O)R′, P(=O)R′R″, S(=O)R′R″, S(=O)2R′, substituted or unsubstituted C1-C18 alklyl, substituted or unsubstituted C2-C18 alkenyl, substituted or unsubstituted C2-C18 alkynyl, substituted or unsubstituted aryl; each of the R′, R″ groups is independently selected from the group consisting of H, OH, NO2, NH2, SH, CN, halogen, =O, C(=O)H, C(=O)CH3, CO2H, CO2CH3, substituted or unsubstituted C1-C18 alkyl, substituted or unsubstituted C1-C18 alkoxy, substituted or unsubstituted C2-C18 alkenyl, substituted or unsubstituted C2-C18 alkynl, substituted or unsubstituted aryl; there may be one or more unsaturations in the hydrocarbon backbone defined by the chain (II) and salts thereof; with the exception of a C16-C24 2-amino-3-hydroxyalkane or a C16-C24 2-amino-3-hydroxyalkene.
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(2008/06/13)

Process to prepare alkyl-ureas from O,S-dimethyl dithiocarbonate
The present invention relates to the preparation of alkyl-ureas, starting from O,S-dimethyl dithiocarbonate, which provides the following steps:A) causing the O,S-dimethyl dithiocarbonate to react with a primary amine of general formula R1NH2 in order to obtain an O-methyl thiocarbamate;B) isomerising the O-methyl thiocarbamate in order to obtain an S-methyl thiocarbamate;C) causing the S-methyl thiocarbamate with a compound of general formula R'R"NH, wherein R' and R" may be equal or different one in respect of the other and of R1 and may be H, R2 or R3, in order to obtain one of the alkyl-ureas of formula (4), (5) or (6).
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(2008/06/13)

A simple synthetic protocol for the protection of amides, lactams, ureas, and carbamates
A new procedure for protecting the amide, lactam, urea, and carbamate NH group with a triphenylmethyl (Tr) group is described. The utility of this method is illustrated with molecules that contain other functional groups. A mild deprotection using trifluoroacetic acid makes this a useful method for attaching amide groups on resin for combinatorial synthesis.
Reddy, Dandu R,Iqbal, Mohamed A,Hudkins, Robert L,Messina-McLaughlin, Patricia A,Mallamo, John P
p. 8063 - 8066
(2007/10/03)

N-ARYLHETEROARYLALKYL IMIDAZOL-2-ONE COMPOUNDS FOR TREATMENT OF CIRCULATORY DISORDERS
A class of N-arylheteroarylalkyl imidazol-2-one compounds is described for use in treatment of circulatory disorders such as hypertension and congestive heart failure. Compounds of particular interest are angiotensin II antagonists of the formula STR1 wherein A is selected from STR2 wherein m is one; wherein R 1 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, 4-methylbutyl, 2-ethylbutyl, n-pentyl, neopentyl, phenyl, methylphenyl, difluorophenyl, benzyl, phenethyl, cyclohexyl, cyclohexylmethyl, cyclohexylethyl, cyclohexanoyl, 1-oxo-2-cyclohexylethyl, benzoyl, 1-oxo-2-phenethyl, 1-oxopropyl, 1-oxobutyl, 1-oxopentyl and 2-hydroxybutyl; wherein R 0 is hydrido; wherein R 2 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, phenyl, benzyl, phenethyl, cyclohexyl, cyclohexylmethyl, propylthio, butylthio, and hydroxyalkyl; wherein each of R 3, R 4, R 6, R 7, R. sup.8, R 9, R 10 and R. sup.11 is hydrido and R 5 must be selected from COOH, SH, P0 3 H. sub.2, SO 3 H, CONHNH 2, CONHNHSO 2 CF 3, OH, STR3 wherein each of R 42 and R 43 is independently selected from chloro, cyano, nitro, trifluoromethyl, methoxycarbonyl and trifluoromethylsulfonyl; or a tautomer thereof or a pharmaceutically-aceptable salt thereof.
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(2008/06/13)

N-substituted imidazol-2-one compounds for treatment of circulatory disorders
A class of N-substituted imidazol-2-one compounds is described for use in treatment of circulatory disorders. Compounds of particular interest are angiotensin II antagonists of the formula STR1 wherein m is one; wherein R1 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, 4-methylbutyl, n-pentyl, neopentyl, phenyl, benzyl, phenethyl, cyclohexyl, cyclohexylmethyl, cyclohexylethyl, cyclohexanoyl, 1-oxo-2-cyclohexylethyl, benzoyl, 1-oxo-2-phenethyl, 1-oxopropyl, 1-oxobutyl, 1-oxopentyl and 2-hydroxybutyl; wherein R0 is selected from hydrido, methyl, fluoro, chloro, monofluoromethyl, difluoromethyl, trifluoromethyl, formyl, carboxyl and dimethoxymethyl; wherein R2 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, phenyl, benzyl, phenethyl, cyclohexyl, cyclohexylmethyl, propylthio, butylthio, and hydroxyalkyl; wherein each of R3, R4, R6, R7, R8, R10 and R11 is hydrido; with the proviso that at least one of R5 and R9 must be selected from COOH, SH, PO3 H2, SO3 H, CONHNH2, CONHNHSO2 CF3, OH, STR2 wherein each of R42 and R43 is independently selected from chloro, cyano, nitro, trifluoromethyl, methoxycarbonyl and trifluoromethylsulfonyl; or a tautomer thereof or a pharmaceutically-acceptable salt thereof. These compounds are particularly useful in treatment or control of hypertension and congestive heart failure.
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(2008/06/13)

Process for the preparation of asymmetrically substituted ureas
Process for the preparation of asymmetrically substituted ureas by reaction of a gaseous mixture of isocyanic acid and ammonia having a temperature of 260° to 600° C. with a primary or secondary amine.
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(2008/06/13)

CATHODIC CLEAVAGE OF THE N-H BOND. ELECTROCHEMICAL REDUCTION OF UREA, N-ACETYLUREA, AND THIOUREA
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Bukhtiarov, A. V.,Mikheev, V. V.,Lebedev, A. V.,Tomilov, A. P.,Kuz'min, O. V.
p. 372 - 378
(2007/10/02)

Herbicidal sulfonamides
Novel N-(heterocyclicaminocarbonyl) substituted thiophene-, furan- and pyrrolesulfonamides, such as N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-6,7-dihydro-5H-thieno-[3,2-b]thiopyran-3-sulfonamide, 4,4-dioxide and N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-6,7-dihydro-5H-thieno[3,2-b]thiopyran-3-sulfonamide, 4,4-dioxide and their method-of-use as herbicides are described.
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(2008/06/13)

Herbicidal thiophenesulfonamides
Thiophenesulfonamides such as N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-3-(isoxazol-3-yl)-2-thiophenesulfonamide are useful as herbicides and plant growth regulants.
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(2008/06/13)

Phenoxazine and phenothiazine dyes and leuco forms thereof
Novel phenoxazine and phenothiazine dyes have the formula STR1 wherein X can be --S-- or --O--; each R can be the same or different and is independently selected from (1) hydrogen, (2) an unsubstituted aryl or alkyl group or these groups substituted by up to four groups selected from alkyl, alkoxy, cyano, hydroxy, halogen, nitro, mercapto, alkylsulfonyl, arylsulfonyl, and Z, where Z is as defined below, wherein all alkyl and alkoxy groups have 1 to 20 carbon atoms; and (3) Z, wherein Z can be STR2 wherein each Q can be the same or different and is independently selected from (1) hydrogen, (2) an unsubstituted aryl or alkyl group or these groups substituted by up to four groups selected from alkyl, alkoxy, cyano, hydroxy, halogen, nitro, mercapto, alkylsulfonyl, arylsulfonyl, and Z, where Z is as defined above, wherein all alkyl and alkoxy groups have 1 to 20 carbon atoms; and R' is the same or different and is independently selected from hydrogen, halogen, alkyl or alkoxy of 1 to 6 carbon atoms or these groups substituted by up to 3 halogen atoms; and A is an anion; with the proviso that R and L can have up to a total of 5 carbonyl and sulfonyl groups, and with the proviso that the average value of a Taft Constant and of a Hammett Constant for the two R groups on at least one 3- or 7-position nitrogen atom is greater than 1.0 for a Taft Constant and greater than +0.1 for a Hammett Constant.
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(2008/06/13)

Phenyl-substituted sulfonamides
This invention relates to 1-benzopyransulfonamides, 1-benzothiopyransulfonamides, 1-benzoxepinsulfonamides and 1-benzothiepinsulfonamides which are useful as plant growth regulants and in particular as herbicides.
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(2008/06/13)

Photochemical model studies on photosensitizing drugs: Sulfonamides and sulfonylureas
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Golpashin,Weiss,Durr
p. 906 - 913
(2007/10/02)

Photochemie von Sulfonamiden und Sulfonylharnstoffen: Ein Beitrag zum Problem der Lichtdermatosen
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Weiss,Duerr,Haas
p. 647 - 649
(2007/10/02)

Studies on the formation of side products in the synthesis of tolbutamide using thin-layer chromatography
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Menzer,Prezewowski,Haug
p. 738 - 739
(2007/10/16)