m-Chloroperbenzoic acid → 2-Amino-5-(5-trifluoromethylpyridin-2-ylsulfinyl)thiazole
Reaction equation
[NH2:1][C:2]1[S:3][C:4]([S:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][N:9]=2)=[CH:5][N:6]=1.ClC1C=CC=C(C(OO)=[O:26])C=1>ClCCl>[NH2:1][C:2]1[S:3][C:4]([S:7]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][N:9]=2)=[O:26])=[CH:5][N:6]=1Participants
Procedure
To a solution of 2-amino-5-(5-trifluoromethylpyridin-2-ylthio)thiazole (0.6 g) in dichloromethane (20 ml) was added portionwise 3-chloroperbenzoic acid (0.6 g) at 5° C. with stirring. The mixture was stirred at 5° C. for 3 hours. The reaction mixture was washed with aqueous sodium bicarbonate and dried over magnesium sulfate. The solvent was concentrated under reduced pressure to give solid. The solid was subjected to column chromatography on silica gel (silica gel 60, 70-230 mesh; Merck: 30 g) and eluted with a mixture of chloroform and methanol (10:1). The fractions containing the objective compound were combined and concentrated under reduced pressure to give 2-amino-5-(5-trifluoromethylpyridin-2-ylsulfinyl)thiazole (0.52 g, yield: 81.9%). mp: 144°-145° C.
Workup
- stirringThe mixture was stirred at 5° C. for 3 hours
- washThe reaction mixture was washed with aqueous sodium bicarbonate
- dry with materialdried over magnesium sulfate
- concentrationThe solvent was concentrated under reduced pressure
- customto give solid
- washeluted with a mixture of chloroform and methanol (10:1)
- additionThe fractions containing the objective compound
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-faaa2f8cb7da41e4a467e7ae572ff0cb
- Source dataset
- uspto-grants-1993_10
- Patent number
- US05256675
Reaction notes
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