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

HRID 1719436

Reaktionsgleichung

Reaktionsgleichung von HRID 1719436
Cl[CH2:2][CH2:3][CH2:4][N:5]([CH:19]([CH3:21])[CH3:20])[S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=1)(=[O:8])=[O:7].[CH3:22][NH:23][CH2:24][CH2:25][C:26]1[CH:35]=[CH:34][C:31]([O:32][CH3:33])=[C:28]([O:29][CH3:30])[CH:27]=1.C(=O)([O-])[O-].[K+].[K+].C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C(C)=CC=CC=1>[CH3:30][O:29][C:28]1[CH:27]=[C:26]([CH2:25][CH2:24][N:23]([CH3:22])[CH2:2][CH2:3][CH2:4][N:5]([CH:19]([CH3:21])[CH3:20])[S:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=2)(=[O:8])=[O:7])[CH:35]=[CH:34][C:31]=1[O:32][CH3:33]

Komponenten

6

Edukt 4

HCID 10796Cesium carbonateHCID 11430Potassium CarbonateHCID 77039N-MethylhomoveratrylamineHCID 23323132N-(3-chloropropyl)-N-(1-methylethyl)-3-trifluoromethylbenzenesulfonamide

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7237O-XyleneLösungsmittel

Versuchsvorschrift

N-(3-chloropropyl)-N-(1-methylethyl)-3-trifluoromethylbenzenesulfonamide (23.4 g, 0.068 mol) and N-methylhomoveratrylamine (13.29 g, 0.068 mol) in xylene (250 mL) containing anhydrous potassium carbonate (4.68 g, 0.034 mol) and cesium carbonate (11.08 g, 0.034 mol) were heated and stirred for 21/2 days. The reaction was cooled, filtered and stripped to provide a gum with a small amount of crystalline material evident. Solution in diethyl ether, filtration of the small amount of solid and concentration of the filtrate provided the crude product (32.91 g). Chromatography first on dry column alumina then silica gel provided the same product as in the preceding example (11.84 g) as a gum.

Aufarbeitung

  1. temperaturewere heated
  2. temperatureThe reaction was cooled
  3. filtrationfiltered
  4. customto provide a gum with a small amount of crystalline material evident
  5. filtrationSolution in diethyl ether, filtration of the small amount of solid and concentration of the filtrate
  6. customprovided the crude product (32.91 g)
  7. customChromatography first on dry column alumina
  8. customsilica gel provided the same product as in the preceding example (11.84 g) as a gum

Quellen und Nachweise

ORD-Eintrag
ord-3f8f5432083648f9a318c5676f5fdfd7
Quelldatensatz
uspto-grants-1985_09
Patentnummer
US04539426

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