Methanol → 1-(3,4-Dichloro-phenyl)-1H-imidazole-4-carboxylic Acid Methyl Ester

반응식

[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[CH:13]=[C:12]([C:14]([OH:16])=[O:15])[N:11]=[CH:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].S(=O)(=O)(O)O.[CH3:22]O>>[CH3:22][O:15][C:14]([C:12]1[N:11]=[CH:10][N:9]([C:4]2[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=2)[CH:13]=1)=[O:16]

참가 물질

반응물 3

HCID 887Methanol

HCID 1118Sulfuric Acid

HCID 234450601-(3,4-Dichlorophenyl)-1H-imidazole-4-carboxylic acid

생성물 1

HCID 690419081-(3,4-Dichloro-phenyl)-1H-imidazole-4-carboxylic Acid Methyl Ester수율 81%

실험 절차

A mixture of 1-(3,4-dichloro-phenyl)-1H-imidazole-4-carboxylic acid (7.0 g, 27 mmol), methanol (150 ml) and conc. sulfuric acid (25 ml) was refluxed for 3 h. The solution was then concentrated to 80 ml and a solution of sodium carbonate (60 g) in H2O at 0° C. (500 ml) was added. Extraction with CH2Cl2, drying of the organic phase and evaporation of the solvent gave a brown residue, which upon triturating with ether gave the title compound (6.0 g, 81%) as a light brown solid. MS: m/e=269.9 (M+).