Water → HCID 21898026, Verbindung

HRID 1839018Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1839018
[CH2:1]([NH2:12])[CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][CH2:10][NH2:11].[S:13](Cl)([C:16]1[C:28]2[CH:27]=[CH:26][CH:25]=[C:21]([N:22]([CH3:24])[CH3:23])[C:20]=2[CH:19]=[CH:18][CH:17]=1)(=[O:15])=[O:14].O>C(#N)C>[NH2:11][CH2:10][CH2:9][CH2:8][O:7][CH2:6][CH2:5][O:4][CH2:3][CH2:2][CH2:1][NH:12][S:13]([C:16]1[C:28]2[C:20](=[C:21]([N:22]([CH3:24])[CH3:23])[CH:25]=[CH:26][CH:27]=2)[CH:19]=[CH:18][CH:17]=1)(=[O:15])=[O:14]

Komponenten

5

Edukt 3

HCID 962WaterHCID 11801Dansyl chlorideHCID 763421-Propanamine, 3,3'-[1,2-ethanediylbis(oxy)]bis-

Produkt 1

HCID 21898026HCID 21898026, VerbindungAusbeute 60,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

4,7-Dioxadecane-1,10-diamine (32.6 g, 0.185 mole) in acetonitrile (100 mL) was chilled in an ice bath. To this was slowly added dropwise dansyl chloride (5 g, 0.0185 mole) dissolved in acetonitrile (60 mL) over a 20 min. period. Stirring in an ice bath was continued for 1.5 hr. The reaction mixture was poured into water (about 300 mL) and extracted with dichloromethane (2×100 mL). The combined extracts were washed with water and dried to give an oil. The oil was purified by column chromatography (silica gel eluting with acetonitrile containing increasing amounts of ethanol) to provide 4.6 g of N-(10-amino-4,7-dioxadecyl)-5-dimethylaminonaphthalene-1-sulfonamide as a viscous oil.

Aufarbeitung

  1. extractionextracted with dichloromethane (2×100 mL)
  2. washThe combined extracts were washed with water
  3. customdried
  4. customto give an oil
  5. customThe oil was purified by column chromatography (silica gel eluting with acetonitrile containing increasing amounts of ethanol)

Quellen und Nachweise

ORD-Eintrag
ord-ec598f9d9ac84ef1bdcdb6468084a0a0
Quelldatensatz
uspto-grants-2004_01
Patentnummer
US06677347B2

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