Imidazole → Dechloroclotrimazole

HRID 429764

Reaction equation

HRID 429764 reaction equation
[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

Participants

5

Reactant 3

HCID 795ImidazoleHCID 6456Trityl chlorideHCID 24758Sodium hydride

Product 1

HCID 618231DechloroclotrimazoleYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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]+.

Workup

  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

Sources & evidence

ORD record
ord-934d32079b2e43a4ba965bf8df977f30
Source dataset
uspto-grants-2001_11
Patent number
US06319922B1

Linked notes

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