Water → N-(2-indanyl)-4-(N-acetyl-N-methylamino)benzenesulfonamide

HRID 260883

Reaktionsgleichung

Reaktionsgleichung von HRID 260883
Cl.[CH2:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH:3]1[NH2:11].[C:12]([N:15]([C:17]1[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1)[CH3:16])(=[O:14])[CH3:13].C([O-])(=O)C.[Na+].O>C(O)C>[CH2:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH:3]1[NH:11][S:23]([C:20]1[CH:19]=[CH:18][C:17]([N:15]([C:12](=[O:14])[CH3:13])[CH3:16])=[CH:22][CH:21]=1)(=[O:25])=[O:24]

Komponenten

6

Edukt 4

HCID 962WaterHCID 1227642-Aminoindan hydrochlorideHCID 2931464-(N-methylacetamido)benzene-1-sulfonyl chlorideHCID 517045Sodium Acetate

Produkt 1

HCID 22918947N-(2-indanyl)-4-(N-acetyl-N-methylamino)benzenesulfonamideAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

2-Indanylamine hydrochloride (9.68 g, 57.1 mmol) was added to a suspension of the 4-(N-acetyl-N-methylamino)benzenesulfonyl chloride (12.84 g, 51.9 mmol) prepared in Preparative Example 12 and sodium acetate (18.73 g) in ethanol (100 ml). The obtained mixture was stirred at room temperature for 3 hours, followed by the addition of water. The obtained mixture was extracted with ethyl acetate. The organic layer was washed with water and a saturated aqueous solution of common salt, dried over magnesium sulfate, and concentrated to give N-(2-indanyl)-4-(N-acetyl-N-methylamino)benzenesulfonamide as a white crystal (16.92 g, 95%). Ethanol (80 ml) and 1N aqueous sodium hydroxide (80 ml) were added to the white crystal. The obtained mixture was heated under reflux overnight, acidified with 1N aqueous hydrochloric acid, adjusted to pH 8 with sodium hydrogencarbonate and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated to precipitate a crystal. This crystal was recovered by filtration and washed with ether to give the title compound as a white crystal (6.79 g, 46%).

Aufarbeitung

  1. extractionThe obtained mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materiala saturated aqueous solution of common salt, dried over magnesium sulfate
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-2cade1d80de54dd4a5d051bbc3917325
Quelldatensatz
uspto-grants-1996_06
Patentnummer
US05530118

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