3,4-Dimethoxyaniline → N-(3,4-Dimethoxyphenyl)-5-isoquinolinesulfonamide

HRID 1090592

Reaktionsgleichung

Reaktionsgleichung von HRID 1090592
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[NH2:6].[CH:12]1[C:21]2[CH:20]=[CH:19][CH:18]=[C:17]([S:22](Cl)(=[O:24])=[O:23])[C:16]=2[CH:15]=[CH:14][N:13]=1.Cl>N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:6][S:22]([C:17]2[C:16]3[CH:15]=[CH:14][N:13]=[CH:12][C:21]=3[CH:20]=[CH:19][CH:18]=2)(=[O:23])=[O:24])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11]

Komponenten

4

Edukt 2

HCID 227703,4-DimethoxyanilineHCID 13116932Isoquinoline-5-sulfonyl chloride hydrochloride

Produkt 1

HCID 15009136N-(3,4-Dimethoxyphenyl)-5-isoquinolinesulfonamideAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

3.06 g of 3,4-dimethoxyaniline was dissolved in 30 ml of pyridine, to the solution was added in small portions 5.28 g of 5-isoquinolinesulfonyl chloride·HCl with stirring under ice cooling, and the mixture was stirred for 30 minutes, and further stirred at a room temperature overnight. After evaporating off the pyridine under a reduced pressure and additing 20 ml of water, the mixture was extracted twice with 50 ml of chloroform/isopropanol (10:1). The extract was dried over magnesium sulfate and evaporated under a reduced pressure to remove the solvent. To the resulting residue was added 20 ml of benzene/chloroform (3:1), and the mixture was slightly warmed and collected to obtain 5.64 g of the title compound as colorless crystals.

Aufarbeitung

  1. stirringthe mixture was stirred for 30 minutes
  2. stirringfurther stirred at a room temperature overnight
  3. customAfter evaporating off the pyridine under a reduced pressure
  4. extractionthe mixture was extracted twice with 50 ml of chloroform/isopropanol (10:1)
  5. dry with materialThe extract was dried over magnesium sulfate
  6. customevaporated under a reduced pressure
  7. customto remove the solvent
  8. additionTo the resulting residue was added 20 ml of benzene/chloroform (3:1)
  9. temperaturethe mixture was slightly warmed
  10. customcollected

Quellen und Nachweise

ORD-Eintrag
ord-240da026da6a44aeb95e0790f4dc6cbd
Quelldatensatz
uspto-grants-1992_01
Patentnummer
US05081246

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