- Method for synthesizing 1-difluoromethyl imidazole and derivative thereof
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The invention discloses a method for synthesizing 1-difluoromethyl imidazole and a derivative thereof. The method is characterized in that ethyl bromodifluoroacetate, a substrate iminazole and a derivative thereof and alkali are dissolved in a reaction solvent, the mixed liquid is heated and stirred, a difluoromethylation reaction happens, and the substrate is benzimidazole, 2-phenyl benzimidazole, 5-nitrobenzimidazole, 5,6-dimethyl benzimidazole, imidazole, 2-methylimidazole and 2-ethyl imidazole. Ethyl bromodifluoroacetate is adopted as a difluoromethylation reagent, no ozone is consumed, environmental friendliness is achieved, the whole reaction condition is mild and aftertreatment is simple.
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Paragraph 0019; 0020
(2017/08/30)
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- Use of fluoroform as a source of difluorocarbene in the synthesis of N-CF2H heterocycles and difluoromethoxypyridines
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Fluoroform is used as a source of difluorocarbene to convert various N-, O-, and C-nucleophiles to their difluoromethylated derivatives. Imidazole, benzimidazole, benztriazole, hydroxypyridines, and their derivatives underwent reaction at moderate temperatures and atmospheric pressure, using potassium hydroxide as base in a two-phase (water/acetonitrile) process to provide moderate to good yields of the respective products. Nitrophenols required addition of a co-solvent (methanol) to obtain good yields of products.
- Thomoson, Charles S.,Wang, Linhua,Dolbier, William R.
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- N -difluoromethylation of imidazoles and benzimidazoles using the ruppert-prakash reagent under neutral conditions
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Direct N-difluoromethylation of imidazoles and benzimidazoles has been achieved using TMS-CF3 (the Ruppert-Prakash reagent) under neutral conditions. Difluoromethylated products were obtained in good-to-excellent yields. Inexpensive, commercial
- Surya Prakash,Krishnamoorthy, Sankarganesh,Ganesh, Somesh K.,Kulkarni, Aditya,Haiges, Ralf,Olah, George A.
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supporting information
p. 54 - 57
(2014/01/23)
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- Multigram synthesis of 1-(difluoromethyl)imidazoles and -benzimidazoles
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An expedient approach to the difluoromethylation of imidazoles and benzimidazoles has been developed. The key feature of the procedure is the gradual generation of the difluoromethylation reagent in the reaction mixture, which is achieved by the simultane
- Levterov, Vadym,Grygorenko, Oleksandr O.,Mykhailiuk, Pavel K.,Tolmachev, Andrey A.
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experimental part
p. 1243 - 1248
(2011/05/14)
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- N-tosyl-S-difluoromethyl-S-phenylsulfoximine: A new difluoromethylation reagent for S-, N-, and C-nucleophiles
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The first α-difluoromethyl sulfoximine compound, 2, was successfully prepared by using the copper(ll)-catalyzed nitrene transfer reaction. Compound 2 was found to be a novel and efficient difluoromethylation reagent for transferring the CF2H gr
- Zhang, Wei,Wang, Fei,Hu, Jinbo
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supporting information; experimental part
p. 2109 - 2112
(2009/09/30)
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- Reactions of some nitrogen heterocycles with chlorodifluoromethane under conditions of phase-transfer catalysis
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Aromatic heterocyclic compounds containing one to four nitrogen atoms react with chlorodifluoromethane in the presence of concentrated aqueous sodium hydroxide and a catalyst, benzyltriethylammonium chloride (TEBAC) in dichloromethane or THF (phase-transfer catalysis, PTC) with formation of N-difluoromethyl substituted derivatives. The process takes place by reaction of N-anions from these heterocycles with difluorocarbene and protonation of difluoromethyl anions thus formed.
- Jończyk, Andrzej,Nawrot, Ewelina,Kisielewski, Micha?
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p. 1587 - 1591
(2007/10/03)
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- Generation of heteroarylium-N-difluoromethylides and heteroaryl-N-difluoromethyl anions and their reactions with electrophiles: Heteroaryl- and heteroarylium-N-difluoromethyl trimethylsilanes and a new heteroaryl-N-trifluoromethane
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Reductive debromination of N-bromodifluoromethyl-4-dimethylaminopyridinium bromide, 1-bromodifluoromethyl-imidazole, 1-methyl-3-bromodifluoromethyl-imidazolium bromide and 1-bromodifluoromethyl-2-methyl-benzimidazole using tetrakis(dimethylamino)ethylene (TDAE) or tris(diethylamido)phosphite leads to new fluorinated carbanionic species, namely heteroarylium-N-difluoromethylides and heteroaryl-N-difluoromethyl anions. In the presence of electrophiles such as benzaldehyde, chlorodiphenylphosphine and chlorotrimethylsilane, the corresponding heteroarylium- and heteroaryl-N-difluoromethylated derivatives, imidazole-N-difluoromethyl-phosphines and -silanes, 2-methyl-benzimidazole-N-difluoromethyltrimethyl-carbinols-phosphines and -silanes were obtained. Similar 4-dimethylaminopyridinium derivatives were synthesized.
- Bissky, German,Roeschenthaler, Gerd-Volker,Lork, Enno,Barten, Jan,Medebielle, Maurice,Staninets, Vasilij,Kolomeitsev, Alexander A.
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p. 173 - 181
(2007/10/03)
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- 1,2,3-Benzothiadiazole derivatives
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Novel 1,2,3-benzothiadiazole derivatives of the formula STR1 in which Het has the meanings set forth in the specification, and addition products thereof with an acid or metal salt are very effective for the control of undesired microorganisms. Novel intermediates of the formulae STR2 in which Het1 and R5 have the meanings given in the specification.
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- Chloropyridylcarbonyl derivatives
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Novel chloropyridylcarbonyl derivatives of the formula STR1 in which Het is STR2 n is 1 or 2, R1 is hydrogen, optionally substituted C1-6 alkyl, optionally substituted C2-6 alkenyl, optionally substituted C3-6 alkynyl, optionally substituted phenyl or optionally substituted pyrimidinyl, and R2 and R3, independently of each other, are hydrogen or C1-4 alkyl, and acid addition salts and metal salt complexes thereof, are outstandingly active as microbicides.
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- FLUORINE-CONTAINING AZOLES. 2. REACTION OF IMIDAZOLE, BENZIMIDAZOLES, AND PERIMIDINES WITH DIFLUOROCARBENE
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The reaction of difluorocarbene, generated from difluorochloromethane in an alkaline medium or from sodium trifluoroacetate in a neutral medium, with imidazole, tetrahydrobenzimidazole, benzimidazoles, and perimidines leads to the production of their N-difluoromethyl-substituted derivatives.
- Poludnenko, V. G.,Didinskaya, O. B.,Pozharskii, A. F.
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p. 422 - 425
(2007/10/02)
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