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

HRID 17857

반응식

HRID 17857 반응식
[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

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

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)+.

후처리

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

출처 및 근거

ORD 기록
ord-49218633147e48a494a0093576d6d942
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741317B2

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