Sodium hydride → N-[3-[[2-(3,4-Dimethoxyphenyl)ethyl]methylamino]propyl]-N-(1-methylethyl)-3-(trifluoromethyl)benzenesulfonamide

HRID 280049

Reaktionsgleichung

Reaktionsgleichung von HRID 280049
[CH:1]([NH:4][S:5]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=1)(=[O:7])=[O:6])([CH3:3])[CH3:2].[H-].[Na+].Cl[CH2:21][CH2:22][CH2:23][N:24]([CH2:26][CH2:27][C:28]1[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[C:30]([O:36][CH3:37])[CH:29]=1)[CH3:25]>CN(C)C=O>[CH3:37][O:36][C:30]1[CH:29]=[C:28]([CH2:27][CH2:26][N:24]([CH3:25])[CH2:23][CH2:22][CH2:21][N:4]([CH:1]([CH3:3])[CH3:2])[S:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:15])[F:16])[CH:9]=2)(=[O:7])=[O:6])[CH:33]=[CH:32][C:31]=1[O:34][CH3:35]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 577693N-(3-Chloropropyl)-3,4-dimethoxy-N-methylphenethylamineHCID 23323137HCID 23323137, Verbindung

Produkt 1

HCID 54053041N-[3-[[2-(3,4-Dimethoxyphenyl)ethyl]methylamino]propyl]-N-(1-methylethyl)-3-(trifluoromethyl)benzenesulfonamideAusbeute 43,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

N-isopropyl-3-trifluoromethylbenzenesulfonamide (5.362 g, 0.02 mol) in dimethylformamide (30 mL) was treated with sodium hydride (60% in mineral oil), (0.802 g) and stirred for 2 hours. Then N-(3-chloropropyl)-3,4-dimethoxy-N-methylphenethylamine (5.436 g, 0.02 mol) was added and the reaction heated overnight. Filtration and removal of solvent provided the crude product (6.95 g). Column chromatography and high pressure liquid chromatography provided the pure product (4.35 g) as a gum. 1H NMR (CDCl3) 1.15 (d, 6, J=3.5H, Me2) 2.25 (s, 3, N-Me) 3.84 (d, 6, (OMe)2) 6.76 (m, 3, Ar) 7.25 (m, 3, Ar).

Aufarbeitung

  1. temperaturethe reaction heated overnight
  2. filtrationFiltration and removal of solvent
  3. customprovided the crude product (6.95 g)

Quellen und Nachweise

ORD-Eintrag
ord-8c9be492c7c24788bc345c98c2a320c9
Quelldatensatz
uspto-grants-1986_05
Patentnummer
US04587360

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