Imidazole → Dechloroclotrimazole

HRID 1855878Notes

Reaction equation

HRID 1855878 reaction equation
P([O-])(OC1C=CC=CC=1)OC1C=CC=CC=1.[NH:17]1[CH:21]=[CH:20][N:19]=[CH:18]1.[C:22]1([C:28]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)O)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>N1C=CC=CC=1>[C:22]1([C:28]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)([C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[N:17]2[CH:21]=[CH:20][N:19]=[CH:18]2)[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 6457TriphenylcarbinolHCID 23418553Diphenoxyphosphanolate

Product 1

HCID 618231DechloroclotrimazoleYield 82.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of pyridine (15 ml), diphenyl phosphite (2.34 g, 10 mmole), imidazole (0.68 g, 10 mmole) and triphenylmethanol (2.08 g, 8 mmole) was refluxed for 3 hours. Pyridine was removed under reduced pressure, and the residue was extracted with dichloromethane. The extract was washed with a 5% aqueous hydroxide solution and water in order, dried and evaporated. Recrystallization of the residue (2.23 g) from acetonitrile gave 2.05 g of 1-triphenylmethylimidazole as colorless needles. Yield, 82.7%. M.P., 221°-223° C.

Workup

  1. temperaturewas refluxed for 3 hours
  2. customPyridine was removed under reduced pressure
  3. extractionthe residue was extracted with dichloromethane
  4. washThe extract was washed with a 5% aqueous hydroxide solution and water in order
  5. customdried
  6. customevaporated
  7. customRecrystallization of the residue (2.23 g) from acetonitrile

Sources & evidence

ORD record
ord-c2fa6fb78e2e44fd863e8a1b7810b6b6
Source dataset
uspto-grants-1980_08
Patent number
US04216333

Reaction notes

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