m-Chloroperbenzoic acid → 2-[[4-(4-Trifluoromethylbenzyloxy)-2-pyridinyl]methylsulfinyl]-1H-thieno[3,4-d]imidazole

HRID 1196626Notes

Reaction equation

HRID 1196626 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[F:12][C:13]([F:39])([F:38])[C:14]1[CH:37]=[CH:36][C:17]([CH2:18][O:19][C:20]2[CH:25]=[CH:24][N:23]=[C:22]([CH2:26][S:27][C:28]3[NH:32][C:31]4=[CH:33][S:34][CH:35]=[C:30]4[N:29]=3)[CH:21]=2)=[CH:16][CH:15]=1>ClCCl>[F:39][C:13]([F:12])([F:38])[C:14]1[CH:37]=[CH:36][C:17]([CH2:18][O:19][C:20]2[CH:25]=[CH:24][N:23]=[C:22]([CH2:26][S:27]([C:28]3[NH:32][C:31]4=[CH:33][S:34][CH:35]=[C:30]4[N:29]=3)=[O:9])[CH:21]=2)=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 144259992-[4-(4-Trifluoromethylbenzyloxy)-2-picolylmercapto]-1H-thieno[3,4-d]imidazole

Product 1

HCID 144260002-[[4-(4-Trifluoromethylbenzyloxy)-2-pyridinyl]methylsulfinyl]-1H-thieno[3,4-d]imidazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 0.5 g (2.5 mmol, 85%) of m-chloroperbenzoic acid in 10 ml of dichloromethane is added dropwise with stirring at 0° to 5° C. to 1.0 g (2.37 mmol) of the title compound from Example 6 in a two-phase mixture of 200 ml of dichloromethane and 100 ml of aqueous KH2PO4 /Na2HPO4 buffer solution (pH=7.5). The organic phase is separated off, shaken with saturated aqueous NaHCO3 solution, dried over MgSO4, clarified over activated charcoal and concentrated. The crystalline evaporation residue is treated with ethyl acetate, filtered off with suction and washed twice with a little ethyl acetate. The colorless crystalline product is dried in vacuo, m.p. 149° C. with decomposition.

Workup

  1. customThe organic phase is separated off
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. additionThe crystalline evaporation residue is treated with ethyl acetate
  5. filtrationfiltered off with suction
  6. washwashed twice with a little ethyl acetate
  7. customThe colorless crystalline product is dried in vacuo, m.p. 149° C. with decomposition

Sources & evidence

ORD record
ord-d774b5f84d5248fdb0281b39d95fd780
Source dataset
uspto-grants-1992_05
Patent number
US05114955

Reaction notes

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