62366-53-4

Usage

Uses

Used in Pharmaceutical Industry:
1H-Imidazole-2-carboxylic acid, 1-methyl-, methyl ester (9CI) is used as an intermediate in the synthesis of various drugs and organic compounds. Its unique chemical properties and anti-inflammatory and antioxidant characteristics make it a valuable component in the development of pharmaceutical products.
Used in Agrochemical Industry:
In the agrochemical sector, 1H-Imidazole-2-carboxylic acid, 1-methyl-, methyl ester (9CI) is utilized in the production of agrochemicals. Its role as a versatile building block allows for the creation of compounds that can be applied in agricultural settings to enhance crop protection and productivity.
Used in Organic Synthesis:
As a key component in organic synthesis, 1H-Imidazole-2-carboxylic acid, 1-methyl-, methyl ester (9CI) is employed in the creation of a wide range of organic compounds. Its reactivity and structural features contribute to the synthesis of various molecules with potential applications in different industries.

Upstream product

• 616-47-7 1-methyl-1H-imidazole 
• 79-22-1 methyl chloroformate 
• 67-56-1 methanol 
• 68-12-2 N,N-dimethyl-formamide 
• 30148-23-3 2-trichloroacetyl-1-methylimidazole 
• 35342-89-3 1-methyl-2-(trimethylsilyl)-1H-imidazole 

Downstream Products

• 129378-60-5 1-methyl-N,N-dimethylimidazole-2-carboxamide 
• 864076-07-3 methyl 4-(4-tert-butoxycarbonylamino-phenyl)-1-methyl-imidazole-2-carboxylate 

Relevant academic research and scientific papers

METHOD FOR PRODUCING IMIDAZOLE-2-CARBOXYLATE DERIVATIVE OR SALT THEREOF

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

Facile preparation of aromatic esters from aromatic bromides with ethyl formate or DMF and molecular iodine via aryllithium

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.

AMINO ACIDS

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.

Transfer of Alkoxycarbonyl from Alkyl Imidazolium-2-carboxylates to Benzyl Alcohol, a Cyclohexanone Enamine and Diethylamine

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.

STUDIES ON THE DILITHIATION OF 1-METHYLIMIDAZOLE. OPTIMISATION OF REACTION CONDITIONS FOR SYNTHESES OF 2,5-DISUBSTITUTED DERIVATIVES

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.