Hydrogen Peroxide → 5-Amino-2-(tert-butylsulfinyl)-4-phenylthiazole
Reaction equation
[NH2:1][C:2]1[S:6][C:5]([S:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[N:4][C:3]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[OH:18]O>C(O)(=O)C>[NH2:1][C:2]1[S:6][C:5]([S:7]([C:8]([CH3:11])([CH3:9])[CH3:10])=[O:18])=[N:4][C:3]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To 5-amino-2-(tert-butylsulfanyl)-4-phenylthiazole (102 mg, 385 μmol) in acetic acid (5.0 ml) was added aqueous hydrogen peroxide (218 μl, 30% wt, 1.9 mmol) dropwise at ambient temperature. After 5 hr the mixture was partitioned between dichloromethane (50 ml) and water (50 ml). The aqueous phase was separated and extracted with dichloromethane (20 ml). The combined organic phases were washed with saturated aqueous sodium bicarbonate, dried over sodium sulfate, filtered and concentrated in vacuo to yield essentially pure 5-amino-2-(tert-butylsulfinyl)-4-phenylthiazole (110 mg, quant.).