Imidazole → 1-[(4-Chlorophenyl)(diphenyl)methyl]-1H-imidazole
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](Cl)([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[NH:22]1[CH:26]=[CH:25][N:24]=[CH:23]1.C(N(CC)CC)C.Cl.C(N(CC)CC)C>C(#N)C.O.C1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:22]2[CH:26]=[CH:25][N:24]=[CH:23]2)=[CH:4][CH:3]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 50 °C
Procedure
156.5 g (0.5 mol) of (p-chlorophenyl)-(diphenyl)-methyl chloride and 34 g (0.5 mol) imidazole are dissolved in 500 ml acetonitrile, with stirring, and 51 g (0.5 mol) triethylamine are added, whereupon separation of triethylamine hydrochloride occurs even at room temperature. In order to complete the reaction, heating at 50°C is carried out for three hours. After cooling, 1 liter of benzene is added and the reaction mixture is stirred, then washed salt-free with water. The benzene solution is dried over anhydrous sodium sulfate, filtered and concentrated by evaporation; giving 167 g of crude 1-[(p-chlorophenyl)-(bisphenyl)-methyl]-imidazole, m.p. 125°C. By recrystallization from 200 ml benzene and 100 ml ligroin, 115 g (= 71% of the thoery) of pure 1-[(p-chlorophenyl) (bis-phenyl)-methyl]-imidazole of m.p. 140°C are obtained.
Workup
- customoccurs even at room temperature
- customthe reaction
- temperatureAfter cooling
- stirringthe reaction mixture is stirred
- dry with materialThe benzene solution is dried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationconcentrated by evaporation
Sources & evidence
- ORD record
- ord-85d18aa42c8d4d0d8f0cd0de632a7dec
- Source dataset
- uspto-grants-1976_01
- Patent number
- US03934022
Reaction notes
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