Imidazole → Clotrimazole

HRID 1855869

Reaktionsgleichung

Reaktionsgleichung von HRID 1855869
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

Komponenten

5

Edukt 3

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

Produkt 1

HCID 2812ClotrimazoleAusbeute 72,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-a535584c4d384c0e9d7126cfb1f6c87a
Quelldatensatz
uspto-grants-1980_08
Patentnummer
US04216333

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