N-Ethyl-p-toluenesulfonamide → N-Ethyl-N-(3-chloropropyl)-p-toluenesulfonamide

HRID 400297

Reaktionsgleichung

Reaktionsgleichung von HRID 400297
[CH2:1]([NH:3][S:4]([C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=1)(=[O:6])=[O:5])[CH3:2].[H-].[Na+].[Cl:16][CH2:17][CH2:18][CH2:19]Cl>CN(C=O)C>[CH2:1]([N:3]([CH2:19][CH2:18][CH2:17][Cl:16])[S:4]([C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=1)(=[O:6])=[O:5])[CH3:2]

Komponenten

5

Edukt 3

HCID 6637N-Ethyl-p-toluenesulfonamideHCID 88811,3-DichloropropaneHCID 24758Sodium hydride

Produkt 1

HCID 14056762N-Ethyl-N-(3-chloropropyl)-p-toluenesulfonamideAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
53 °C

Versuchsvorschrift

To N-ethyl-p-toluenesulfonamide (5.01 g, 0.0251 mol) in DMF (50 mL) in a dry flask is added sodium hydride (80% in oil, 0.93 g, 0.031 mol). After gas evolution subsides, 1,3-dichloropropane (22.48 g, 0.199 mol) is added. The mixture is heated at 53° C. for 10 h then cooled and poured into ice water (300 mL), which is extracted twice with ether. The combined extracts are washed with 1% sodium bisulfite, water (3×), and brine. Removal of solvent by rotary evaporation then Kugelrohr distillation gives crude product, which is chromatographed on silica gel (30% hexane/CHCl3) to furnish 2.91 g product (42%) NMR (CDCl3) δ 1.15 (t, 3H), 1.9-2.2 (m, 2H), 2.44 (s, 3H), 3.11-3.35 (m, 4H), 3.6 (t, 2H), 7.3 (d, 2H), 7.74 (d, 2H).

Aufarbeitung

  1. temperaturethen cooled
  2. extractionis extracted twice with ether
  3. washThe combined extracts are washed with 1% sodium bisulfite, water (3×), and brine
  4. customRemoval of solvent
  5. customby rotary evaporation
  6. distillationKugelrohr distillation
  7. customgives crude product, which
  8. customis chromatographed on silica gel (30% hexane/CHCl3)

Quellen und Nachweise

ORD-Eintrag
ord-472d92ff17464d39a01578a1f37db1b3
Quelldatensatz
uspto-grants-1998_10
Patentnummer
US05827894

Verknüpfte Notizen

Wird geladen…