m-Chloroperbenzoic acid → 2-Amino-4-methyl-5-(2-pyridylsulfinyl)thiazole

HRID 1656990Notes

Reaction equation

HRID 1656990 reaction equation
[NH2:1][C:2]1[S:3][C:4]([S:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)=[C:5]([CH3:7])[N:6]=1.ClC1C=CC=C(C(OO)=[O:23])C=1>C(Cl)(Cl)Cl.ClCCl>[NH2:1][C:2]1[S:3][C:4]([S:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)=[O:23])=[C:5]([CH3:7])[N:6]=1

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 189547352-Amino-4-methyl-5-(2-pyridylthio)thiazole

Product 1

HCID 157291892-Amino-4-methyl-5-(2-pyridylsulfinyl)thiazoleYield 52.2%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

A mixture of 2-amino-4-methyl-5-(2-pyridylthio)thiazole (1.7 g) and 3-chloroperbenzoic acid (1.8 g) in a mixture of chloroform (20 ml) and dichloromethane (50 ml) was stirred at 5° C. for 3.5 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-4-methyl-5-(2-pyridylsulfinyl)thiazole (0.95 g, yield: 52.2 %). mp: 190°-193° C. (dec.)

Workup

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

Sources & evidence

ORD record
ord-3d40e69cefd048dc94fa9772c97cb315
Source dataset
uspto-grants-1993_10
Patent number
US05256675

Reaction notes

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