Imidazole → Clotrimazole

HRID 1855877Notes

Reaction equation

HRID 1855877 reaction equation
P(OC1C=CC=CC=1)(OC1C=CC=CC=1)OC1C=CC=CC=1.[NH:23]1[CH:27]=[CH:26][N:25]=[CH:24]1.[Cl:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[C:35]([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)O>C1(C)C=CC=CC=1>[Cl:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[C:35]([C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[N:23]1[CH:27]=[CH:26][N:25]=[CH:24]1

Participants

5

Reactant 3

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

Product 1

HCID 2812ClotrimazoleYield 81.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of toluene (20 ml), triphenyl phosphite (2.07 g, 6.7 mmole), imidazole (1.09 g, 16 mmole) and o-chlorophenyldiphenylmethanol (2.95 g, 10 mmole) obtained in Example 1 (B) was refluxed for 4 hours. The reaction mixture was treated in the same manner as in Example 3 to give 2.80 g of 1-(o-chlorophenyldiphenylmethyl)imidazole. Yield, 81%. M.P., 142°-143° C.

Workup

  1. temperaturewas refluxed for 4 hours
  2. additionThe reaction mixture was treated in the same manner as in Example 3

Sources & evidence

ORD record
ord-31a2c723676a433aa00f0e259134e0ae
Source dataset
uspto-grants-1980_08
Patent number
US04216333

Reaction notes

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