1-(3,4-Dichlorophenyl)-1H-imidazole-4-carboxylic acid → HCID 23444980, compound

HRID 433578Notes

Reaction equation

HRID 433578 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[CH:13]=[C:12]([C:14](O)=[O:15])[N:11]=[CH:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[CH:13]=[C:12]([CH2:14][OH:15])[N:11]=[CH:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

3

Reactant 1

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

Product 1

HCID 23444980HCID 23444980, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
5 °C

Procedure

1-(3,4-Dichloro-phenyl)-1H-imidazole-4-carboxylic acid (20.0 g, 77.8 mmol) was treated with 1M BH3 THF complex (100 ml) and refluxed for 2 h. The mixture was cooled to 5° C. and MeOH (20 ml) was added slowly. After evaporation of all volatiles the residue was taken up in 2N HCl solution (100 ml) and refluxed for 2 h. After filtration the hot aqueous phase was slowly treated with 2N NaOH solution until pH 10. On cooling the title compound crystallizes as a white material (12.2 g, 65%). Mp. 146-147° C. (H2O), MS: m/e=242 (M+).

Workup

  1. temperaturerefluxed for 2 h
  2. customAfter evaporation of all volatiles the residue
  3. temperaturerefluxed for 2 h
  4. filtrationAfter filtration the hot aqueous phase
  5. additionwas slowly treated with 2N NaOH solution until pH 10
  6. temperatureOn cooling the title compound
  7. customcrystallizes as a white material (12.2 g, 65%)

Sources & evidence

ORD record
ord-3fd3da5ac90247e28dc7f58dfb98f399
Source dataset
uspto-grants-2003_12
Patent number
US06667335B2

Reaction notes

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