Imidazole → 1-(2-chloro-4-fluorophenyl)-2-(1H-imidazol-1-yl)ethanone hydrochloride

HRID 1390616Notes

Reaction equation

HRID 1390616 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:6]=1[Cl:12])=[O:4].O(CC)CC.[NH:18]1[CH:22]=[CH:21][N:20]=[CH:19]1.CN(C)C=O>O>[ClH:12].[Cl:12][C:6]1[CH:7]=[C:8]([F:11])[CH:9]=[CH:10][C:5]=1[C:3](=[O:4])[CH2:2][N:18]1[CH:22]=[CH:21][N:20]=[CH:19]1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 3283Diethyl EtherHCID 6228DimethylformamideHCID 125933352-Chloro-4-fluorophenacyl bromide

Product 1

HCID 203326301-(2-chloro-4-fluorophenyl)-2-(1H-imidazol-1-yl)ethanone hydrochloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of 78.7 parts of 2-bromo-1-(2-chloro-4-fluorophenyl)ethanone in 140 parts of 1,1'-oxybisethane are added carefully 106.4 parts of 1H-imidazole. Upon completion, there are added 180 parts of N,N-dimethylformamide and the whole is stirred for 2 hours at 50° C. After the addition of water, the product is extracted twice with trichloromethane. The combined extracts are washed three times with water, dried, filtered and evaporated. The residue is converted into the hydrochloride salt in 4-methyl-2-pentanone, 2,2'-oxybispropane and 2-propanol. The salt is filtered off and crystallized from a mixture of ethanol and 2,2'-oxybispropane, yielding 1.5 parts of 1-(2-chloro-4-fluorophenyl)-2-(1H-imidazol-1-yl)ethanone hydrochloride; mp. 197.4° C.

Workup

  1. extractionthe product is extracted twice with trichloromethane
  2. washThe combined extracts are washed three times with water
  3. customdried
  4. filtrationfiltered
  5. customevaporated
  6. filtrationThe salt is filtered off
  7. customcrystallized from a mixture of ethanol and 2,2'-oxybispropane

Sources & evidence

ORD record
ord-0dd4b8396aeb493ba0b32b956272542d
Source dataset
uspto-grants-1979_02
Patent number
US04139540

Reaction notes

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