Triethylamine → ethyl 1-methyl-1H-imidazole-2-carboxylate
Reaction equation
[CH2:1]([N:3]([CH2:6]C)[CH2:4]C)[CH3:2].CC1[NH:10]C=CN=1.Cl[C:15]([O:17][CH2:18][CH3:19])=[O:16]>C(#N)C>[CH2:18]([O:17][C:15]([C:4]1[N:3]([CH3:6])[CH:1]=[CH:2][N:10]=1)=[O:16])[CH3:19]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -30 °C
Procedure
Triethyl amine (50 mL) is added to a solution of methyl imidazol (16.3 g, 199 mmol) in acetonitrile (100 mL), then it is cooled to −30° C. A solution of ethyl chloroformate (31 mL, 328 mmol) in acetonitrile (50 mL) is added slowly keeping the temperature bellow 10° C. The reaction mixture is concentrated and diluted in water and extracted with chloroform, dried with MgSO4 anh, filtered and evaporated. Recrystallisation from ether yields 1-Methyl-1H-imidazole-2-carboxylic acid ethyl ester as an orange oil (15.5 g, 51%).
Workup
- custombellow 10° C
- concentrationThe reaction mixture is concentrated
- additiondiluted in water
- extractionextracted with chloroform
- dry with materialdried with MgSO4 anh
- filtrationfiltered
- customevaporated
- customRecrystallisation from ether
Sources & evidence
- ORD record
- ord-bebdb0b3cfac4872989acd5b1884f0a9
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08362018B2
Reaction notes
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