Imidazole → HCID 6481671, compound

HRID 325988Notes

Reaction equation

HRID 325988 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6](=[O:9])[CH2:7]Br)=[CH:4][CH:3]=1.C(Cl)Cl.[NH:15]1[CH:19]=[CH:18][N:17]=[CH:16]1>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6](=[O:9])[CH2:7][C:16]2[NH:15][CH:19]=[CH:18][N:17]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 6344Dichloromethane2×HCID 68303p-Chlorophenacyl bromide

Product 1

HCID 6481671HCID 6481671, compoundYield 77.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

89.2 g 4-chlorophenacyl bromide is dissolved in 170 ml chloroform (or methylene chloride) and the solution is then added dropwise to a solution of 156 g imidazole in 600 ml chloroform (or methylene chloride, as the case may be) while maintaining the reaction mixture at about 0° to 5° C. Thereafter the mixture is continually stirred at this temperature for 4 hours, the solvent is distilled off in a rotation evaporator and the residue is treated with water. After filtering off and drying the precipitate and recrystallizing it in toluene one obtains 65 g p-chlorophenacyl imidazole or 1-(4-chlorophenyl)-2-(1H-imidazol-1-yl)-1-ethanone in the form of colorless crystals having a melting point of 158° to 160° C.

Workup

  1. temperaturewhile maintaining the reaction mixture at about 0° to 5° C
  2. distillationthe solvent is distilled off in a rotation evaporator
  3. additionthe residue is treated with water
  4. filtrationAfter filtering off
  5. customdrying the precipitate
  6. customrecrystallizing it in toluene one

Sources & evidence

ORD record
ord-b1853d3f19684f4795b3531148835f38
Source dataset
uspto-grants-1984_04
Patent number
US04443612

Reaction notes

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