Imidazole → Dechloroclotrimazole

HRID 1358797Notes

Reaction equation

HRID 1358797 reaction equation
[C:1](Cl)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:21]1[CH:25]=[CH:24][N:23]=[CH:22]1.C(N(CC)CC)C>C(Cl)Cl>[C:1]([N:21]1[CH:25]=[CH:24][N:23]=[CH:22]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 6456Trityl chlorideHCID 8471Triethylamine

Product 1

HCID 618231DechloroclotrimazoleYield 90.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of trityl chloride (5.58 g, 20.0 mmol.) in dry methylene chloride (100 ml) cooled down to 0° C. and stirred under Ar, was added dropwise over 1.5 hours a solution of imidazole (1.36 g, 20.0 mmol.) and triethylamine (2.7 mml, 20 mmol.) in 50 ml dry methylene chloride. At the end of the addition, the reaction mixture was allowed to warm up to room temperature and stirred under Ar at that temperature overnight. The reaction mixture was then washed with 20ml of a 10% solution of ammonium chloride, then with 20 ml of distilled water. The organic phase was dried over magnesium sulfate and evaporated in vacuo to yield quantitatively a white solid. Recrystallization from methylene chloride/hexanes yielded 5.60 g of (5) (yield=90% after recrystallization).

Workup

  1. additionAt the end of the addition
  2. stirringstirred under Ar at that temperature overnight
  3. washThe reaction mixture was then washed with 20ml of a 10% solution of ammonium chloride
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. customevaporated in vacuo
  6. customto yield quantitatively a white solid
  7. customRecrystallization from methylene chloride/hexanes

Sources & evidence

ORD record
ord-7cda9e8240654114955f0b7362b57585
Source dataset
uspto-grants-2003_07
Patent number
US06596857B1

Reaction notes

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