Imidazole → Dechloroclotrimazole

HRID 2248380Notes

Reaction equation

HRID 2248380 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[C:6]1([C:12](Cl)([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.O>C(OCC)(=O)C>[C:12]([N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1)([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 962WaterHCID 6456Trityl chloride

Product 1

HCID 618231DechloroclotrimazoleYield 41.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 23.5 g (0.35 mole) of imidazole in 425 mL of ethyl acetate was added 48.0 g (0.32 mole) of triphenylmethyl chloride. The mixture was stirred for 20 hours and then 500 mL of water was added. After being stirred for an additional 2 hours, the mixture was filtered. The ethyl acetate layer was separated, dried (MgSO4) and concentrated. Recrystallization of the residue from xylene gave 41 g of white crystals, mp 222°-225° C..

Workup

  1. stirringAfter being stirred for an additional 2 hours
  2. filtrationthe mixture was filtered
  3. customThe ethyl acetate layer was separated
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customRecrystallization of the residue from xylene

Sources & evidence

ORD record
ord-c99a01b8f53040c59621ee539c33eaff
Source dataset
uspto-grants-1991_08
Patent number
US05039691

Reaction notes

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