p-Toluenesulfonic acid → N-(6-chloro-pyrazin-2-yl)-4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide

HRID 484691노트

반응식

HRID 484691 반응식
[OH:1][C:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[S:5](=[O:13])(=[O:12])[N:4]([CH3:14])[C:3]=1[C:15]([NH:17][C:18]1[CH:23]=CC=CC=1)=[O:16].NC1C=[N:29][CH:28]=[C:27]([Cl:31])[N:26]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C(C)=CC=CC=1>[Cl:31][C:27]1[N:26]=[C:18]([NH:17][C:15]([C:3]2[N:4]([CH3:14])[S:5](=[O:12])(=[O:13])[C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[C:2]=2[OH:1])=[O:16])[CH:23]=[N:29][CH:28]=1

참가 물질

5

반응물 3

HCID 6101p-Toluenesulfonic acidHCID 1184582-Amino-6-ChloropyrazineHCID 546847802H-1,2-Benzothiazine-3-carboxamide, 4-hydroxy-2-methyl-N-phenyl-, 1,1-dioxide

생성물 1

HCID 54703135N-(6-chloro-pyrazin-2-yl)-4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide수율 23%

시약·촉매·용매 1

HCID 7237O-Xylene용매

실험 절차

1.0 g (3 mmols) of 4-hydroxy-2-methyl-N-phenyl-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide were refluxed with 1.3 g (10 mmols) of 2-amino-6-chloro-pyrazine and 0.1 g of p-toluenesulfonic acid in 250 ml of xylene for 72 hours. After cooling, the reaction mixture was washed with 2N hydrochloric acid and then with water, then dried and concentrated by evaporation in vacuo. The residue was purified column chromatography (Merck silicagel 60; particle size: 0.2-0.5 mm; eluant: chloroform/ethanol 90:10) and yielded 0.25 g (23% of theory) of N-(6-chloro-pyrazin-2-yl)-4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide.

후처리

  1. temperatureAfter cooling
  2. washthe reaction mixture was washed with 2N hydrochloric acid
  3. dry with materialwith water, then dried
  4. concentrationconcentrated by evaporation in vacuo
  5. customThe residue was purified column chromatography (Merck silicagel 60; particle size: 0.2-0.5 mm; eluant: chloroform/ethanol 90:10)

출처 및 근거

ORD 기록
ord-5af9c3448c424fe09485da41cedb0b72
출처 데이터셋
uspto-grants-1985_08
특허 번호
US04533664

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