m-Chloroperbenzoic acid → HCID 15729151, compound

HRID 2380595Notes

Reaction equation

HRID 2380595 reaction equation
[C:1]([NH:4][C:5]1[S:6][C:7]([S:10][C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=2)=[CH:8][N:9]=1)(=[O:3])[CH3:2].ClC1C=CC=C(C(OO)=[O:26])C=1>ClCCl.CN(C)C=O>[C:1]([NH:4][C:5]1[S:6][C:7]([S:10]([C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=2)=[O:26])=[CH:8][N:9]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 15729149HCID 15729149, compound

Product 1

HCID 15729151HCID 15729151, compoundYield 71.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-acetylamino-5-(4-aminophenylthio)thiazole (6.6 g) in a mixture of dichloromethane (300 ml) and N,N-dimethylformamide (50 ml) was dropwise added the solution of 3-chloroperbenzoic acid (5.9 g) in dichloromethane (100 ml) at 5° C. with stirring. The mixture was stirred at 5° C. for 2 hours with stirring. The reaction mixture was concentrated under reduced pressure and the residue was poured into 10% aqueous sodium bicarbonate. The solution was extracted with a mixture of tetrahydrofuran and ethyl acetate (1:1), washed with saturated aqueous sodium chloride and dried over magnesium sulfate. The solvent was concentrated under reduced pressure to give 2-acetylamino-5-(4-aminophenylsulfinyl)thiazole (5.0 g, yield: 71.1%).

Workup

  1. stirringThe mixture was stirred at 5° C. for 2 hours
  2. stirringwith stirring
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionthe residue was poured into 10% aqueous sodium bicarbonate
  5. extractionThe solution was extracted with a mixture of tetrahydrofuran and ethyl acetate (1:1)
  6. washwashed with saturated aqueous sodium chloride
  7. dry with materialdried over magnesium sulfate
  8. concentrationThe solvent was concentrated under reduced pressure

Sources & evidence

ORD record
ord-6361f503022e473aa79a9ff8333f97cf
Source dataset
uspto-grants-1994_11
Patent number
US05369107

Reaction notes

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