m-Chloroperbenzoic acid → HCID 15729179, compound

HRID 2380618Notes

Reaction equation

HRID 2380618 reaction equation
[NH2:1][C:2]1[S:3][C:4]([S:7][C:8]2[CH:13]=[CH:12][C:11]([NH:14][S:15]([CH3:18])(=[O:17])=[O:16])=[CH:10][CH:9]=2)=[CH:5][N:6]=1.ClC1C=CC=C(C(OO)=[O:27])C=1>C(Cl)(Cl)Cl>[NH2:1][C:2]1[S:3][C:4]([S:7]([C:8]2[CH:9]=[CH:10][C:11]([NH:14][S:15]([CH3:18])(=[O:17])=[O:16])=[CH:12][CH:13]=2)=[O:27])=[CH:5][N:6]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 15729163HCID 15729163, compound

Product 1

HCID 15729179HCID 15729179, compoundYield 92.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a mixture of 2-amino-5-(4-methanesulfonylaminophenylthio)thiazole (2.0 g) in chloroform (100 ml) was added dropwise the solution of 3-chloroperbenzoic acid (1.6 g) in chloroform (50 ml) at 5° C. under ice cooling with stirring. The mixture was stirred at 5° C. for 2.5 hours. The reaction mixture was washed with aqueous sodium bicarbonate and the precipitates were collected by filtration. The solid was washed with aqueous sodium bicarbonate and water, dried in vacuo to give 2-amino-5-(4-methanesulfonylaminophenylsulfinyl)thiazole (1.95 g, yield: 92.6%).

Workup

  1. stirringThe mixture was stirred at 5° C. for 2.5 hours
  2. washThe reaction mixture was washed with aqueous sodium bicarbonate
  3. filtrationthe precipitates were collected by filtration
  4. washThe solid was washed with aqueous sodium bicarbonate and water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-32d03df6b5014ed381117da58450d4b7
Source dataset
uspto-grants-1994_11
Patent number
US05369107

Reaction notes

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