Imidazole → Clotrimazole

HRID 1855870

Reaction equation

HRID 1855870 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>C1(C)C=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 74.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of toluene (20 ml), diphenyl 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 (A) was refluxed for 4 hours. After cooling to room temperature, the reaction mixture was washed with a 5% aqueous potassium hydroxide solution (20 ml). The toluene layer was separated, washed with water, dried and evaporated to give a crystalline mass. Recrystallization from acetonitrile gave 2.57 g of 1-(o-chlorophenyldiphenylmethyl)imidazole. Yield, 74.5%. M.P., 142°-143° C.

Workup

  1. temperaturewas refluxed for 4 hours
  2. washthe reaction mixture was washed with a 5% aqueous potassium hydroxide solution (20 ml)
  3. customThe toluene layer was separated
  4. washwashed with water
  5. customdried
  6. customevaporated
  7. customto give a crystalline mass
  8. customRecrystallization from acetonitrile

Sources & evidence

ORD record
ord-6b51a589ee774ba8b2f4acd0943309c5
Source dataset
uspto-grants-1980_08
Patent number
US04216333

Linked notes

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