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

HRID 2198782Notes

Reaction equation

HRID 2198782 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>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

4

Reactant 2

HCID 795ImidazoleHCID 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 wate (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. The hydrochloride salt from acetone/methanol had a m.p. of 172.5°-174° C.

Workup

  1. additionThe resulting solution was poured into wate (1500 ml)
  2. filtrationthe precipitate filtered off
  3. washwashed well with water and hexane
  4. washChromatography of the product on silica gel (1 Kg), eluting with 7% methanol in methylene chloride

Sources & evidence

ORD record
ord-a50cc8d588b043378c8dac45d3283058
Source dataset
uspto-grants-1982_11
Patent number
US04359475

Reaction notes

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