m-Chloroperbenzoic acid → 2-Amino-5-(3-pyridylsulfinyl)thiazole

HRID 1656998Notes

Reaction equation

HRID 1656998 reaction equation
[NH2:1][C:2]1[S:3][C:4]([S:7][C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)=[CH:5][N:6]=1.ClC1C=CC=C(C(OO)=[O:22])C=1>ClCCl.C(Cl)(Cl)Cl>[NH2:1][C:2]1[S:3][C:4]([S:7]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)=[O:22])=[CH:5][N:6]=1

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 15729196HCID 15729196, compound

Product 1

HCID 157291972-Amino-5-(3-pyridylsulfinyl)thiazoleYield 37.2%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 2-amino-5-(3-pyridylthio)thiazole (3.0 g) in a mixture of dichloromethane (100 ml) and chloroform (100 ml) was added dropwise the solution of 3-chloroperbenzoic acid (3.4 g) in dichloromethane (50 ml) 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 the aqueous layer was extracted with a mixture of tetrahydrofuran and ethyl acetate (1:1), washed with aqueous saturated sodium chloride and dried over magnesium sulfate. The solvent was concentrated under reduced pressure and the residue was recrystallized from ethanol to give 2-amino-5-(3-pyridylsulfinyl)thiazole (1.2 g, yield: 37.2%). mp: 178°-179° C.

Workup

  1. stirringThe mixture was stirred at 5° C. for 3 hours
  2. washThe reaction mixture was washed with aqueous sodium bicarbonate
  3. extractionthe aqueous layer was extracted with a mixture of tetrahydrofuran and ethyl acetate (1:1)
  4. washwashed with aqueous saturated sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. concentrationThe solvent was concentrated under reduced pressure
  7. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-fe2a48e13967411e87c5135f2105cef8
Source dataset
uspto-grants-1993_10
Patent number
US05256675

Reaction notes

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