4-Methoxybenzenesulfonyl chloride → 4-methoxy-n-Decylsulfamoylbenzene

HRID 129360

Reaktionsgleichung

Reaktionsgleichung von HRID 129360
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9](Cl)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[CH2:13]([NH2:23])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]>N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9](=[O:11])(=[O:10])[NH:23][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:5][CH:4]=1

Komponenten

4

Edukt 2

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 8916Decylamine

Produkt 1

HCID 52013694-methoxy-n-DecylsulfamoylbenzeneAusbeute 66,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

Commercially available 4-methoxybenzenesulfonylchloride (Aldrich; 25 g, 0.12 moles) is added portionwise to a solution of decylamine (Kodak; 19 g, 0.12 moles) in pyridine (75 mL). The heterogeneous reaction mixture is stirred overnight at room temperature and poured into dilute HCl/ice water (1.5 L). After stirring 30 minutes, the light orange solid is isolated by filtration, washed with water and air dried. Recrystallization from ethanol (Norite) affords 26.3 g (66% yield) of the desired product as golden platelets, mp 53°-54.5° C. NMR (CDCl3) d 0.8-0.95 (t, 3H's); 1.1-1.6 (m, 16H's); 2.8-3.0 (t, 2H's); 3.9 (s, 3H's); 6.95-7.0 (d, 2H's); 7.75-7.85 (d, 2H's).

Aufarbeitung

  1. stirringAfter stirring 30 minutes
  2. customthe light orange solid is isolated by filtration
  3. washwashed with water and air
  4. customdried
  5. customRecrystallization from ethanol (Norite)

Quellen und Nachweise

ORD-Eintrag
ord-35cc5ce59e954d9bae0a3b8762b75909
Quelldatensatz
uspto-grants-1995_11
Patentnummer
US05468587

Verknüpfte Notizen

Wird geladen…