Imidazole → 4-(4-Chlorophenyl)-1-(imidazol-1-yl)butan-2-one

HRID 354590Notes

Reaction equation

HRID 354590 reaction equation
Cl[CH2:2][C:3](=[O:13])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=1.[NH:14]1[CH:18]=[CH:17][N:16]=[CH:15]1.O>CN(C)C=O>[Cl:12][C:9]1[CH:10]=[CH:11][C:6]([CH2:5][CH2:4][C:3](=[O:13])[CH2:2][N:14]2[CH:18]=[CH:17][N:16]=[CH:15]2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 962WaterHCID 128164651-Chloro-4-(4-chlorophenyl)butan-2-one

Product 1

HCID 110103354-(4-Chlorophenyl)-1-(imidazol-1-yl)butan-2-oneYield 79.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-Chloro-4-(4-chlorophenyl)-2-butanone (110 g) was added portionwise over half an hour to a stirred suspension of imidazole (175 g) in dimethylformamide (150 ml) at 0° C. and the mixture stirred overnight at ambient temperature. The resulting solution was poured into water (1500 ml) with seeding at the first sign of turbidity, and the precipitate filtered off and washed well with water and hexane. Chromatography of the product on silica gel (1 Kg.), eluting with 7% methanol in methylene chloride gave 100 g of 1-[4-(4-chlorophenyl)butan-2-on-1-yl]imidazole.

Workup

  1. filtrationthe precipitate filtered off
  2. washwashed well with water and hexane
  3. washChromatography of the product on silica gel (1 Kg.), eluting with 7% methanol in methylene chloride

Sources & evidence

ORD record
ord-7b869343bf794572aeabfe544ed4dde3
Source dataset
uspto-grants-1983_03
Patent number
US04375474

Reaction notes

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