Imidazole → 1-[(4-Fluorophenyl)diphenylmethyl]-1H-imidazole

HRID 1580851Notes

Reaction equation

[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[F:6][C:7]1[CH:12]=[CH:11][C:10]([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:9][CH:8]=1.C(N(CC)CC)C.Cl.C(N(CC)CC)C>C(#N)C.C1C=CC=CC=1>[F:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=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:11][CH:12]=1

Participants

Conditions

Temperature: 50 °C

Procedure

34 g (0.5 mol) imidazole are dissolved at room temperature, with stirring, in a solution of 148.25 g, (0.5 mol) of (p-fluorophenyl)-(diphenyl)-methyl chloride in 500 ml acetonitrile. Following this, 51 g (0.5 mol) triethylamine are added dropwise; triethylamine hydrochloride separates immediately upon heating. For completion of the reaction, the mixture is heated at 50°C for 3 hours. After cooling, the reaction mixture is stirred together with 1 liter of benzene and washed salt-free with water. The benzene solution is dried over anhydrous sodium sulfate, filtered and concentrated by evaporation; giving 148 g of crude 1-[(p-fluorophenyl)-(bisphenyl)-methyl]-imidazole of m.p. 146°C (= 91% of the theory). By recrystallization from 300 ml benzene and 50 ml ligroin, the m.p. rises to 148°C.

Workup

additionare added dropwise
temperatureupon heating
customFor completion of the reaction
temperatureAfter cooling
washwashed salt-free with water
dry with materialThe benzene solution is dried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated by evaporation

Sources & evidence

ORD record: ord-4ecf77ee7bba4d56ab0a89d4ec90b044
Source dataset: uspto-grants-1976_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03934022

Reaction notes

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