- METHOD FOR PRODUCING IMIDAZOLE-2-CARBOXYLATE DERIVATIVE OR SALT THEREOF
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PROBLEM TO BE SOLVED: To develop a method for stably obtaining an imidazole-2-carboxylate derivative or salt thereof at a high yield regardless of a scale of a reaction and an addition time of a reagent, and to efficiently produce an industrially useful imidazole-2-carboxylate derivative or salt thereof. SOLUTION: There is provided a method for producing an imidazole-2-carboxylate derivative or salt thereof including: an adding step of adding an imidazole derivative or salt thereof and triethylamine into a mixed liquid of a chloroformic ester derivative and acetonitrile under the condition of -45°C to 10°C; and a reacting step of reacting the imidazole derivative or salt thereof with the chloroformic ester to obtain the imidazole-2-carboxylate derivative or salt thereof. SELECTED DRAWING: None COPYRIGHT: (C)2017,JPOandINPIT
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Paragraph 0059
(2017/11/01)
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- Facile preparation of aromatic esters from aromatic bromides with ethyl formate or DMF and molecular iodine via aryllithium
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Various aromatic bromides were treated with n-BuLi and subsequently with ethyl formate, followed by the reaction with ethanol and molecular iodine in the presence of K2CO3 to provide the corresponding aromatic ethyl esters in good yields. Moreover, aromatic bromides could be transformed into the corresponding aromatic methyl esters in good yields by the treatment with n-BuLi and subsequently with DMF, followed by the reaction with methanol, molecular iodine, and K2CO3. Some aromatics could be also converted into the corresponding aromatic esters in good yields by the treatment with n-BuLi, and subsequently with ethyl formate or DMF, followed by the reaction with molecular iodine and K2CO3. The present reactions offer a novel route for the transition-metal-free, carbon-monoxide-free, and therefore environmentally benign one-pot conversion of aromatic bromides and aromatics into aromatic esters.
- Ushijima, Sousuke,Moriyama, Katsuhiko,Togo, Hideo
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experimental part
p. 4701 - 4709
(2012/07/28)
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- AMINO ACIDS
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Compounds of formula (I): Z’ -CO-A-B-NH-Z (I) wherein: Z is H or an amino protecting group; Z’ is OH, a protected or activated hydroxyl group or C1; A is an optionally substituted C5-6 arylene group; and B is an optionally substituted C5-6 arylene group.
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Page/Page column 61-62
(2008/06/13)
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- Transfer of Alkoxycarbonyl from Alkyl Imidazolium-2-carboxylates to Benzyl Alcohol, a Cyclohexanone Enamine and Diethylamine
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Alkylimidazole-2-carboxylates may be alkylated with methyl triflate to give the corresponding N-methylimidazolium salts.These salts react with benzyl alcohol in the presence of 1,4-diazabicyclooctane, with 1-(pyrrolidin-1-yl)cyclohexene and with diethylamine to give benzyl alkyl carbonates, an enamino ester and a urethane respectively; in one case a tetrahedral intermediate is observed.The corresponding phenyl ester was consumed without attack by benzyl alcohol at the carbonyl group.A 2-cyanoimidazolium salt underwent similar ill-defined consumption whereas a 2-dimethylaminocarbonyl derivative remained unchanged. 2-Methylsulfonylimidazolium salts suffered attack by benzyl alcohol at the ring C-2.
- Bakhtiar, Cuross,Smith, Edward H.
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p. 239 - 244
(2007/10/02)
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- STUDIES ON THE DILITHIATION OF 1-METHYLIMIDAZOLE. OPTIMISATION OF REACTION CONDITIONS FOR SYNTHESES OF 2,5-DISUBSTITUTED DERIVATIVES
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Reaction of 1-methylimidazole with an excess of n-butyllithium yields the 2,5-dilithio intermediate.The extent of dilithiation is dependent on the solvent, reaction time, temperature and molar ratio of the lithiating agent to the substrate.Use of a chelating agent for Li(+) decreases the reaction time, temperature and molar excess of the alkyllithium required for high-yielding dilithiation.Syntheses via the dilithio intermediate of 2,5-bis(hydroxydiphenylmethyl)- (3) and 2,5-bis(methylthio)-1-methylimidazole (5), of 1-methyl-5-trimethylsilylimidazole (8), and (in poor yields) of 1-methylimidazole-2,5-dicarboxylic acid (9) and methyl 1-methylimidazole-2,5-dicarboxylate (10) are reported.
- Carpenter, Andrew J.,Chadwick, Derek J.,Ngochindo Raphael I.
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p. 1913 - 1941
(2007/10/02)
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