Imidazole → Dechloroclotrimazole

HRID 429764

Reaktionsgleichung

Reaktionsgleichung von HRID 429764
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[H-].[Na+].[C:8]1([C:14](Cl)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>CN(C=O)C>[C:14]([N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Komponenten

5

Edukt 3

HCID 795ImidazoleHCID 6456Trityl chlorideHCID 24758Sodium hydride

Produkt 1

HCID 618231DechloroclotrimazoleAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Imidazole (10.0 g, 146.9 mmol) was added to sodium hydride (60% dispersion in mineral oil, pre-washed in hexane, 6.5 g, 161.6 mmol) in DMF (200 ml), triphenylmethylchloride (41.0 g, 146.9 mmol) was then added and the reaction mixture stirred at room temperature for 18 h. The mixture was poured onto ice and the solid precipitate formed filtered off and partitioned between water and dichloromethane. The organic phase was washed with brine and dried over sodium sulphate and concentrated in vacuo to give the title compound (37.8 g, 83%). 1H NMR (CDCl3) δ 7.42-7.03 (1H, m). MS (ES) m/e 311 [M+H]+.

Aufarbeitung

  1. additionwas then added
  2. additionThe mixture was poured onto ice
  3. customthe solid precipitate formed
  4. filtrationfiltered off
  5. custompartitioned between water and dichloromethane
  6. washThe organic phase was washed with brine
  7. dry with materialdried over sodium sulphate
  8. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-934d32079b2e43a4ba965bf8df977f30
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06319922B1

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