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

HRID 433591Notes

Reaction equation

HRID 433591 reaction equation
[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]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 234450601-(3,4-Dichlorophenyl)-1H-imidazole-4-carboxylic acid

Product 1

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

Procedure

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+).

Workup

  1. temperaturewas refluxed for 3 h
  2. concentrationThe solution was then concentrated to 80 ml
  3. additiona solution of sodium carbonate (60 g) in H2O at 0° C. (500 ml) was added
  4. extractionExtraction with CH2Cl2
  5. customdrying of the organic phase and evaporation of the solvent
  6. customgave a brown residue, which
  7. customupon triturating with ether

Sources & evidence

ORD record
ord-d436a3806aaa4390bf8d225c1218c38e
Source dataset
uspto-grants-2003_12
Patent number
US06667335B2

Reaction notes

Loading…