Ammonia → 2-Amino-3,4-dihydro-3-oxo-2H-1,4-benzothiazine

HRID 1033398노트

반응식

HRID 1033398 반응식
[NH3:1].Cl[CH:3]1[C:8](=[O:9])[NH:7][C:6]2[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=2[S:4]1>C(Cl)Cl>[NH2:1][CH:3]1[C:8](=[O:9])[NH:7][C:6]2[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=2[S:4]1

참가 물질

4

반응물 2

HCID 222AmmoniaHCID 122185992H-1,4-Benzothiazin-3(4H)-one, 2-chloro-

생성물 1

HCID 107974522-Amino-3,4-dihydro-3-oxo-2H-1,4-benzothiazine수율 41%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Anhydrous ammonia gas was bubbled for one hour through a suspension of 500 mg (2.5 mmol) of 2-chloro-3,4-dihydro-3-oxo-2H-1,4-benzothiazine (prepared by the method of Worley, et al; J. Org. Chem., 40, 1731-1734 (1975)) in 5 mL of methylene chloride. The mixture was filtered through Celite and the filtrate evaporated under vacuum. The residue was triturated with 20 mL of chloroform, filtered and the filtrate evaporated under vacuum. Purification by flash chromatography on silica, eluting with ethyl acetate, afforded 185 mg (1.0 mmol, 41%) of the product. 1H NMR (200 MHz, CDCl3): 2.00 (br s,2H), 4.68 (br s,1H), 6.9-7.4 (m,4H), 9.05 (br s,1H). FAB-MS: calculated for C8H8N2OS 180; found 181 (M+h,54%).

후처리

  1. customprepared by the method of Worley, et al
  2. filtrationThe mixture was filtered through Celite
  3. customthe filtrate evaporated under vacuum
  4. customThe residue was triturated with 20 mL of chloroform
  5. filtrationfiltered
  6. customthe filtrate evaporated under vacuum
  7. customPurification by flash chromatography on silica
  8. washeluting with ethyl acetate

출처 및 근거

ORD 기록
ord-73d192cde12747f089285a0b7ed28b38
출처 데이터셋
uspto-grants-1994_05
특허 번호
US05310737

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