Imidazole → HCID 19429447, compound

HRID 1078383Notes

Reaction equation

HRID 1078383 reaction equation
Cl[CH2:2][C:3]([CH3:17])([CH3:16])[C:4]([NH:6][CH:7]([C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1)[CH3:8])=[O:5].[NH:18]1[CH:22]=[CH:21][N:20]=[CH:19]1>>[Cl:15][C:12]1[CH:13]=[CH:14][C:9]([CH:7]([NH:6][C:4](=[O:5])[C:3]([CH3:17])([CH3:16])[CH2:2][N:18]2[CH:22]=[CH:21][N:20]=[CH:19]2)[CH3:8])=[CH:10][CH:11]=1

Participants

3

Reactant 2

HCID 795ImidazoleHCID 19429435HCID 19429435, compound

Product 1

HCID 19429447HCID 19429447, compound

Conditions

Temperature
125 °C

Procedure

A mixture of 3-chloro-N-[1-(4-chlorophenyl)ethyl]-2,2-dimethylpropionamide (5.0 g) and imidazole (6.2 g) was heated at 125° C. with stirring for 6 hours. Excess imidazole was removed by azeotropic distillation with toluene under reduced pressure. The residue was dissolved in 5M hydrochloric acid and washed with dichloromethane. The acid layer was basified with 5M sodium hydroxide solution and extracted with dichloromethane. The combined extracts were washed with water, dried and evaporated to give N-[1-(4-chlorophenyl)ethyl]-3-(imidazol-1-yl)-2,2-dimethylpropionamide which was used directly in (c) below.

Workup

  1. customExcess imidazole was removed by azeotropic distillation with toluene under reduced pressure
  2. dissolutionThe residue was dissolved in 5M hydrochloric acid
  3. washwashed with dichloromethane
  4. extractionextracted with dichloromethane
  5. washThe combined extracts were washed with water
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-729daac6ea3046b19f2bf3b1b030aea1
Source dataset
uspto-grants-1996_08
Patent number
US05547972

Reaction notes

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