Imidazole → Clotrimazole

HRID 1855876Notes

Reaction equation

HRID 1855876 reaction equation
P([O-])(OC1C=CC=CC=1)OC1C=CC=CC=1.[NH:17]1[CH:21]=[CH:20][N:19]=[CH:18]1.[Cl:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:29]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)O>C1C=CC=CC=1>[Cl:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:29]([C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[N:17]1[CH:21]=[CH:20][N:19]=[CH:18]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 298659(2-Chlorophenyl)diphenylmethanolHCID 23418553Diphenoxyphosphanolate

Product 1

HCID 2812ClotrimazoleYield 78.9%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of benzene (20 ml), diphenyl phosphite (5.62 g, 24 mmole), imidazole (2.45 g, 36 mmole) and o-chlorophenyldiphenylmethanol (2.95 g, 10 mmole) obtained in Example 1 (B) was refluxed for 8 hours. The reaction mixture was treated in the same manner as in Example 2 to give 2.72 g of 1-(o-chlorophenyldiphenylmethyl)imidazole. Yield, 79%. M.P., 143°-144° C.

Workup

  1. temperaturewas refluxed for 8 hours
  2. additionThe reaction mixture was treated in the same manner as in Example 2

Sources & evidence

ORD record
ord-ac921daf6eae4adab7e4a6dd17fcdd90
Source dataset
uspto-grants-1980_08
Patent number
US04216333

Reaction notes

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