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

HRID 484691Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 484691
[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

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7237O-XyleneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-5af9c3448c424fe09485da41cedb0b72
Quelldatensatz
uspto-grants-1985_08
Patentnummer
US04533664

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