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

HRID 484691ノート

反応式

HRID 484691 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 7237O-Xylene溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-5af9c3448c424fe09485da41cedb0b72
出典データセット
uspto-grants-1985_08
特許番号
US04533664

反応ノート

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