Imidazole → Clotrimazole

HRID 1855869Notes

Reaction equation

HRID 1855869 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 72.8%

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 (A) was refluxed for 8 hours. After cooling, the reaction mixture was washed with a 5% aqueous potassium hydroxide solution (20 ml). The benzene layer was separated, washed with water, dried over magnesium sulfate and evaporated. Recrystallization of the crystalline residue from acetonitrile gave 2.51 g of 1-(o-chlorophenyldiphenylmethyl)imidazole. Yield, 73%. M.P., 142°-143° C.

Workup

  1. temperaturewas refluxed for 8 hours
  2. temperatureAfter cooling
  3. washthe reaction mixture was washed with a 5% aqueous potassium hydroxide solution (20 ml)
  4. customThe benzene layer was separated
  5. washwashed with water
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. customRecrystallization of the crystalline residue from acetonitrile

Sources & evidence

ORD record
ord-a535584c4d384c0e9d7126cfb1f6c87a
Source dataset
uspto-grants-1980_08
Patent number
US04216333

Reaction notes

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