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

HRID 2380590Notes

Reaction equation

HRID 2380590 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[NH2:12][C:13]1[S:14][CH:15]=[C:16]([CH2:18][S:19][C:20]2[CH:25]=[CH:24][C:23]([NH2:26])=[CH:22][CH:21]=2)[N:17]=1>ClCCl.CN(C)C=O>[NH2:12][C:13]1[S:14][CH:15]=[C:16]([CH2:18][S:19]([C:20]2[CH:25]=[CH:24][C:23]([NH2:26])=[CH:22][CH:21]=2)=[O:9])[N:17]=1

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 15729148HCID 15729148, compound

Product 1

HCID 189547392-Amino-4-(4-aminophenylsulfinylmethyl)thiazoleYield 86.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3-chloroperbenzoic acid (4.9 g) in dichloromethane (100 ml) was dropwise added to a solution of 2-amino-4-(4-aminophenylthiomethyl)thiazole (5.1 g) in a mixture of dichloromethane (200 ml) and N,N-dimethylformamide (10 ml) at 5° C. with stirring. The mixture was stirred at 5° C. for 1.5 hours with stirring. The precipitates were collected by filtration, washed with ethyl acetate and dried in vacuo to give solid. The solid was recrystallized from ethanol to give 2-amino-4- (4-aminophenylsulfinylmethyl)thiazole (4.70 g, yield: 86.3%).

Workup

  1. stirringThe mixture was stirred at 5° C. for 1.5 hours
  2. stirringwith stirring
  3. filtrationThe precipitates were collected by filtration
  4. washwashed with ethyl acetate
  5. customdried in vacuo
  6. customto give solid
  7. customThe solid was recrystallized from ethanol

Sources & evidence

ORD record
ord-229d8e0b7ddc45868dafe8a15fba33c0
Source dataset
uspto-grants-1994_11
Patent number
US05369107

Reaction notes

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