- Process for the preparation of N-substituted lactams
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The invention relates to a process for the preparation of N-substituted lactams by reaction of a lactam, which is unsubstituted on the nitrogen, with an organic halide in the presence of at least one solid-liquid phase transfer catalyst, such as a quaternary ammonium salt, and of at least one solid inorganic base, such as an alkali metal hydroxide, and in the absence of solvent. By this process, N-substituted lactams are obtained with good yields and high purity. The absence of solvent makes possible a considerable gain in productivity and an improvement in safety and in regard for the environment.
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- Syntheses of long-chain quaternary ammonium salts from fatty alcohols by microwave irradiation
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The phase-transfer catalysts, long-chain quaternary ammonium salts, were rapidly synthesized from fatty alcohols by the reactions with hydrogen halides in the presence of trialkyl amines under microwave irradiation. The catalysts could be widely applied in a variety of quick and new organic reactions, whether by conventional heating or under microwave irradiation. The reaction efficiencies under microwave irradiation were higher than those obtained with conventional heating.
- Jiang,Hu,Pang,Yuan
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p. 847 - 850
(2007/10/03)
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- N-allyl-lactams as crystallization inhibitors
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Crystallization of active material in spraying of an aqueous solution of certain specified fungicides is retarded by incorporation therein of an N-alkyl-lactam of the formula STR1 in which R represents alkyl having 6 to 18 carbon atoms and n represents the numbers 3, 4 or 5.
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- N-alkyl-lactams as crystallization inhibitors
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In the spraying of an aqueous liquor comprising at least one of 1-(4-chlorophenyl)-4,4-dimethyl-3-(1,2,4-triazol-1-yl-methyl)-pentan-3-ol and 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-ol, the improvement which comprises including in the liquor an N-alkyl-lactam of the formula STR1 in which R represents alkyl having 8 to 18 carbon atoms and n represents the numbers 3, 4 or 5,
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- Facilitated transport of two model steroids by esters and amides of clofibric acid
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A series of novel dermal penetration enhancers, esters and amides of clofibric acid, was synthesized. The permeation parameters and skin retention of two steroids (hydrocortisone-21-acetate and betamethasone-17-valerate) in propylene glycol were studied with athymic nude mouse skin by in vitro diffusion cell techniques in the presence of the novel enhancer compounds. Isopropyl myristate, dimethyl lauramide, and 1-dodecylazacycloheptan-2-one (laurocapram, Azone) were used as control enhancers. The most satisfactory enhancement of both the ester and amide series was observed with clofibric acid octyl amide; coadministration increased skin retention of hydrocortisone acetate after 24 h by 3.5-fold and that of betamethasone valerate by 2.9- fold. Diffusion cell receptor concentrations increased 51.6- and 10.3-fold, respectively, during the same time period. However, the enhancer compound in this case was applied to the skin 1 h prior to each of the steroids. The amide analogues were more effective than the equivalent ester compounds of the same carbon chain length. The best enhancer compounds (2c, 3d, 3e, and 3f) were nonirritating to athymic mouse skin in vivo.
- Michniak,Chapman,Seyda
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p. 214 - 219
(2007/10/02)
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- Solid formulations
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New solid formulations of A) at least one agrochemical active compound, B) at least one additive from the groups mentioned in the description, C) at least one dispersant, D) at least one carrier and E) if appropriate, further active compounds and/or additives, a process for preparing the solid formulations and their use for treating plants. A new device for preparing new granules.
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- Process for the production of 1-n-dodecylazacycloheptan-2-one
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There is disclosed a method for the production of 1-n-dodecylazacycloheptan-2-one by reacting caprolactam with 1-bromododecane in the presence of a phase transfer catalyst under anhydrous conditions using a nonpoisonous hydrocarbon as solvent. The method is a one-pot synthesis employing solid-liquid phase transfer catalysis.
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- Process for preparing 1-dodecylazacycloheptane-2-one
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Disclosed is a process for preparing 1-dodecylazacyclo-heptane-2-one, the process comprising reacting azacylcloheptane-2-one with dodecyl halide in a substantially non-aqueous system in the presence of a phase-transfer catalyst represented by the formula STR1 wherein R1, R2, R3 and R4 are alkyl or aralkyl, or two or three of the groups R1, R2, R3 and R4, when taken together with nitrogen to which they are attached, form a heterocyclic group (in which case the remaining one or two of the groups being alkyl or aralkyl) and X? is a univalent anion.
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- Toxicity screening of N-alkylazacycloheptan-2-one derivatives in cultured human skin cells: Structure-toxicity relationships
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A number of N-alkylazacycloheptan-2-one derivatives, with the hydrocarbon chain lengths systematically varied from C2 to C16, were tested for their possible skin toxic effects. For this purpose, three in vitro cytotoxicity assays were used: (1) inhibition of proliferation of cultured human fibroblasts and keratinocytes: (2) inhibition of collagen contraction by human fibroblasts; and (3) cell morphology changes in confluent cultures of human fibroblasts and keratinocytes. With all assays used, the toxicity of N-alkylazacycloheptan-2-one derivatives increased from C2 to C8, remained constant at a hydrocarbon chain length between C8 and C14, and subsequently decreased with increasing alkyl chain length. A similar trend has been observed for flux enhancement of nitroglycerine in the presence of these N-alkylazacycloheptan-2-one derivatives, suggesting that with these compounds a parallelism exists between skin cell toxicity and penetration enhancing capacity. Since for practical use it is preferable to find a balance between skin toxicity and the penetration enhancement effect of a particular enhancer, it would be advisable to do QSAR studies of this kind with a number of congeners of a particular compound in order to optimize the choice. In this particular case, further modification of the N-alkylazacycloheptan-2-one structure might lead to an even better choice than the often propagated dodecyl derivative.
- Ponec,Haverkort,Soei,Kempenaar,Brussee,Bodde
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p. 738 - 741
(2007/10/02)
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- Process for the preparation of 1-substituted aza-cycloalkan-2-ones
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A process for the preparation of 1-substituted azacycloalkan-2-ones of the formula I STR1 in which R, m and n have the meanings indicated by reaction of corresponding 1-trimethylsilylazacycloalkan-2-ones with alkali metal alcoholate or alkali metal oxide and then alkylation of the alkali metal salts which are formed.
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- Method of improved pest control
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The disclosure describes a method for improved plant pest control comprising contacting a plant or plant pest with a composition comprising an effective amount of a plant pesticide and an effective delivery enhancing amount of compound having the structural formula STR1 wherein R' is H or a lower alkyl group having 1-4 carbon atoms, m is 3-7, n is 0-17 and R is --CH3, STR2 where R" is H or halogen, with the proviso that if m is 3 and R is CH3, then n is 5-17. Typical plant pesticides include insecticides, fungicides, herbicides, rodenticides, nematicides molluscicides and acaricides. The preferred penetration enhancing compound is 1-n-dodecylaza cycloheptan-2-one.
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- Method of synthesis of 1-dodecylazacycloheptan-2-one
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In a method of synthesis of 1-substituted azacycloalkan-2-ones with primary alkyl halides and aralkyl halides as alkylating agents, the improvement comprising carrying out the N-alkylation in the presence of a phase transfer catalyst having the structural formula STR1 where X is suitable anion; and R1, R2, R3 and R4 are each alkyl or aralkyl groups having 1-18 carbon atoms, or R2, R3 and R4 can form a part of a heterocyclic ring, with the proviso that the combined total of carbon atoms is between 16 and 40.
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- Method of treatment of inflammation
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There is disclosed a method of treatment of inflammation in humans and animals comprising contacting the inflamed area with an effective, anti-inflammatory amount of 1-dodecylazacycloheptan-2-one.
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