m-Chloroperbenzoic acid → HCID 15729150, compound

HRID 1656948Notes

Reaction equation

HRID 1656948 reaction equation
[NH2:1][C:2]1[S:3][C:4]([S:7][C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=2)=[CH:5][N:6]=1.ClC1C=CC=C(C(OO)=[O:23])C=1>C(Cl)(Cl)Cl.CN(C)C=O>[NH2:1][C:2]1[S:3][C:4]([S:7]([C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=2)=[O:23])=[CH:5][N:6]=1

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 18954726HCID 18954726, compound

Product 1

HCID 15729150HCID 15729150, compoundYield 87.5%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-amino-5-(4-aminophenylthio)thiazole (4.0 g) in a mixture of chloroform (140 ml) and N,N-dimethylformamide (20 ml) was dropwise added the solution of 3-chloroperbenzoic acid (4.65 g) in chloroform (50 ml) at 5° C. with stirring. The mixture was stirred at 5° C. for 4 hours. The precipitates were collected by filtration, washed with 10% aqueous sodium bicarbonate and water. The solid was dried in vacuo to give 2-amino-5-(4-aminophenylsulfinyl)thiazole (3.75 g, yield: 87.5%). mp: 173°-175° C.

Workup

  1. stirringThe mixture was stirred at 5° C. for 4 hours
  2. filtrationThe precipitates were collected by filtration
  3. washwashed with 10% aqueous sodium bicarbonate and water
  4. customThe solid was dried in vacuo

Sources & evidence

ORD record
ord-251a1b304b7146dc89fa6e5db218be73
Source dataset
uspto-grants-1993_10
Patent number
US05256675

Reaction notes

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