m-Chloroperbenzoic acid → 2-Amino-5-(2-pyridylsulfinyl)thiazole

HRID 2380604Notes

Reaction equation

HRID 2380604 reaction equation
Cl.Cl.[NH2:3][C:4]1[S:5][C:6]([S:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)=[CH:7][N:8]=1.ClC1C=CC=C(C(OO)=[O:24])C=1>C(Cl)(Cl)Cl>[NH2:3][C:4]1[S:5][C:6]([S:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)=[O:24])=[CH:7][N:8]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 189547342-Amino-5-(2-pyridylthio)thiazole dihydrochloride

Product 1

HCID 101307512-Amino-5-(2-pyridylsulfinyl)thiazoleYield 106.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of 2-amino-5-(2-pyridylthio)thiazole dihydrochloride (4.0 g) in chloroform (100 ml) was dropwise added the solution of 3-chloroperbenzoic acid (5.0 g) in chloroform (100 ml) at 5° C. with stirring. The mixture was stirred at 5° C. for 1.5 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: 100 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-(2-pyridylsulfinyl)thiazole (3.4 g, yield: 78.9%).

Workup

  1. stirringThe mixture was stirred at 5° C. for 1.5 hours
  2. washThe reaction mixture was washed with aqueous sodium bicarbonate
  3. dry with materialdried over magnesium sulfate
  4. concentrationThe solvent was concentrated under reduced pressure
  5. customto give solid
  6. washeluted with a mixture of chloroform and methanol (10:1)
  7. additionThe fractions containing the objective compound
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a6802daa7ec84565920f5839a2e2bf89
Source dataset
uspto-grants-1994_11
Patent number
US05369107

Reaction notes

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