2-Aminothiophenol → 2-phenyl-4H-1,4-benzothiazin-3-one

HRID 17857

Reaction equation

HRID 17857 reaction equation
[C:1]1([CH:7]2[CH2:12][NH:11][C:10]3[CH:13]=[CH:14][CH:15]=[CH:16][C:9]=3[S:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[O:18]C(=O)C(Br)C1C=CC=CC=1.NC1C=CC=CC=1S>CN(C=O)C.CCOC(C)=O.O>[C:1]1([CH:7]2[C:12](=[O:18])[NH:11][C:10]3[CH:13]=[CH:14][CH:15]=[CH:16][C:9]=3[S:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 3

HCID 87132-AminothiophenolHCID 137806Benzeneacetic acid, alpha-bromo-, methyl esterHCID 130715212-Phenyl-3,4-dihydro-2H-1,4-benzothiazine

Product 1

HCID 2347682-phenyl-4H-1,4-benzothiazin-3-one

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Phenyl-3,4-dihydro-2H-1,4-benzothiazine: To bromo-phenyl-acetic acid methyl ester (4.88 g, 21 mmol) in DMF (15 mL) under an argon atmosphere was added 2-amino-benzenethiol (2.3 mL, 21 mmol) and the reaction was stirred at rt overnight. The reaction mixture was diluted with EtOAc (5 mL) and water (50 mL) and the crude product was collected by filtration, washed with warm EtOAc, and dried to give 2-phenyl-4H-1,4-benzothiazin-3-one as a white solid (3.49 g). LC/MS m/z 242 (M+H)+. To this intermediate (3.48 g, 14.4 mmol) in THF (50 mL) under an argon atmosphere was added 1M BH3.THF (50 mL, 50 mmol) and the reaction was stirred at rt overnight. The reaction was quenched with 1N HCl and extracted with ether. The combined organic fractions were dried over MgSO4 and concentrated. 201A was purified by recrystallization from hot EtOAc/hexanes to yield pale pink crystals (1.5 g). LC/MS m/z 228.2 (M+H)+.

Workup

  1. filtrationthe crude product was collected by filtration
  2. washwashed with warm EtOAc
  3. customdried

Sources & evidence

ORD record
ord-49218633147e48a494a0093576d6d942
Source dataset
uspto-grants-2010_06
Patent number
US07741317B2

Linked notes

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