Imidazole → Clotrimazole

HRID 1855874Notes

Reaction equation

HRID 1855874 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)O.P(OC1C=CC=CC=1)(OC1C=CC=CC=1)OC1C=CC=CC=1.[NH:44]1[CH:48]=[CH:47][N:46]=[CH:45]1>C(C(C)=O)C(C)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[N:44]1[CH:48]=[CH:47][N:46]=[CH:45]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 7540Triphenyl phosphiteHCID 298659(2-Chlorophenyl)diphenylmethanol

Product 1

HCID 2812ClotrimazoleYield 86.9%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of o-chlorophenyldiphenylmethanol (29.5 g) obtained in Example 1 (B), triphenyl phosphite (24.8 g), imidazole (12.3 g) and methyl isobutyl ketone (150 ml) was heated at 100° C. for 5 hours. The reaction mixture was treated in the same manner as in Example 6 to give 30.0 g of 1-(o-chlorophenyldiphenylmethyl)imidazole. Yield, 87%. M.P., 143°-144° C.

Workup

  1. additionThe reaction mixture was treated in the same manner as in Example 6

Sources & evidence

ORD record
ord-cfb5452162e74a67adaf2f9e338b8f88
Source dataset
uspto-grants-1980_08
Patent number
US04216333

Reaction notes

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