m-Chloroperbenzoic acid → 2-Amino-4-(4-aminophenylsulfonylmethyl)thiazole

HRID 1656944Notes

Reaction equation

HRID 1656944 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][S:8]([C:10]2[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=2)=[O:9])[N:6]=1.ClC1C=CC=C(C(OO)=[O:25])C=1>CN(C)C=O>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][S:8]([C:10]2[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=2)(=[O:25])=[O:9])[N:6]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 189547392-Amino-4-(4-aminophenylsulfinylmethyl)thiazole

Product 1

HCID 157291472-Amino-4-(4-aminophenylsulfonylmethyl)thiazoleYield 95.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-amino-4-(4-aminophenylsulfinylmethyl)thiazole (2.8 g) in N,N-dimethylformamide (30 ml) was added portionwise the 3-chloroperbenzoic acid (2.6 g) at 5° C. with stirring. The mixture was stirred at room temperature for 2 hours and then the solution was poured into ice-water. The precipitates were collected by filtration, washed with aqueous sodium bicarbonate, washed with water and dried in vacuo to give 2-amino-4-(4-aminophenylsulfonylmethyl)thiazole (2.85 g, yield 95.6%). mp: 204°-208° C. (dec.)

Workup

  1. stirringThe mixture was stirred at room temperature for 2 hours
  2. filtrationThe precipitates were collected by filtration
  3. washwashed with aqueous sodium bicarbonate
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-cc9218e9e2c243d28aed8f2f8111e8a6
Source dataset
uspto-grants-1993_10
Patent number
US05256675

Reaction notes

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