Dimethylformamide → HCID 15729194, compound

HRID 1656995Notes

Reaction equation

HRID 1656995 reaction equation
[NH2:1][C:2]1[S:3][C:4]([S:7][C:8]2[C:13]([OH:14])=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:5][N:6]=1.ClCCl.CN(C)C=[O:21].ClC1C=CC=C(C(OO)=O)C=1>C(Cl)(Cl)Cl>[NH2:1][C:2]1[S:3][C:4]([S:7]([C:8]2[C:13]([OH:14])=[CH:12][CH:11]=[CH:10][N:9]=2)=[O:21])=[CH:5][N:6]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6344DichloromethaneHCID 70297m-Chloroperbenzoic acidHCID 15729193HCID 15729193, compound

Product 1

HCID 15729194HCID 15729194, compoundYield 12.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a mixture of 2-amino-5-(3-hydroxypyridin-2-ylthio)thiazole (4.6 g) in a mixture of chloroform (100 ml), dichloromethane (200 ml) and N,N-dimethylformamide (50 ml) was added dropwise the solution of 3-chloroperbenzoic acid (4.3 g) in chloroform (50 ml) at 5° C. with stirring. The mixture was stirred at room temperature for 5 hours. The reaction mixture was extracted with aqueous diluted hydrochloric acid and the aqueous layer was washed with ethyl acetate. The aqueous layer was adjusted to pH 5.7 using sodium bicarbonate and extracted with a mixture of tetrahydrofuran and ethyl acetate (1:1). The organic layer was washed with aqueous saturated sodium chloride 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: 250 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-(3-hydroxypyridin-2-ylsulfinyl)thiazole (0.65 g, yield: 12.2%). mp: 155-158° C. (dec.) IR (Nujol): 3300, 3150, 1620, 1565, 1515, 1300 cm-1

Workup

  1. stirringThe mixture was stirred at room temperature for 5 hours
  2. extractionThe reaction mixture was extracted with aqueous diluted hydrochloric acid
  3. washthe aqueous layer was washed with ethyl acetate
  4. extractionextracted with a mixture of tetrahydrofuran and ethyl acetate (1:1)
  5. washThe organic layer was washed with aqueous saturated sodium chloride
  6. dry with materialdried over magnesium sulfate
  7. concentrationThe solvent was concentrated under reduced pressure
  8. customto give solid
  9. washeluted with a mixture of chloroform and methanol (10:1)
  10. additionThe fractions containing the objective compound
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fa483ec9246e484ca9c53c023d763da5
Source dataset
uspto-grants-1993_10
Patent number
US05256675

Reaction notes

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