Imidazole → 1-[(3-Chlorophenyl)(diphenyl)methyl]-1H-imidazole

HRID 1580852Notes

Reaction equation

HRID 1580852 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[Cl:6][C:7]1[CH:8]=[C:9]([C:13](Cl)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:10]=[CH:11][CH:12]=1.O>C(#N)C.CN(C)C=O>[Cl:6][C:7]1[CH:8]=[C:9]([C:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)[CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 962WaterHCID 12195715HCID 12195715, compound

Product 1

HCID 159166051-[(3-Chlorophenyl)(diphenyl)methyl]-1H-imidazole

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

27.2 g (0.4 mol) imidazole and 62.8 g (0.2 mol) of (m-chlorophenyl)-(diphenyl)-methyl chloride are heated to 80°C for 4 hours in 150 ml of dry acetonitrile and 50 ml dimethyl formamide. The solvent is then drawn off and the residue is digested with water to remove the imidazole hydrochloride. The residue is taken up in methylene chloride, dried over sodium sulfate, and the viscous oil remaining behind after the distilling off of the solvent is recrystallized from cyclohexane. 52 g (75% of the theory) of 1-[(m-chlorophenyl)-(bisphenyl)-methyl]-imidazole of m.p. 101°C are obtained.

Workup

  1. customto remove the imidazole hydrochloride
  2. dry with materialdried over sodium sulfate
  3. customis recrystallized from cyclohexane

Sources & evidence

ORD record
ord-ee700f5914b3463a979a059e0d865d4a
Source dataset
uspto-grants-1976_01
Patent number
US03934022

Reaction notes

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