Tetrahydrofuran → 5,6-dichloro-N-[3-(dimethylamino)propyl]-N-methylpyridine-3-sulfonamide

HRID 81672

Reaktionsgleichung

Reaktionsgleichung von HRID 81672
C(N(CC)CC)C.[CH3:8][N:9]([CH3:15])[CH2:10][CH2:11][CH2:12][NH:13][CH3:14].O1CCCC1.[Cl:21][C:22]1[CH:23]=[C:24]([S:29](Cl)(=[O:31])=[O:30])[CH:25]=[N:26][C:27]=1[Cl:28]>O>[Cl:21][C:22]1[CH:23]=[C:24]([S:29]([N:13]([CH2:12][CH2:11][CH2:10][N:9]([CH3:15])[CH3:8])[CH3:14])(=[O:31])=[O:30])[CH:25]=[N:26][C:27]=1[Cl:28]

Komponenten

6

Edukt 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 783021,3-Propanediamine, N1,N1,N3-trimethyl-HCID 47369115,6-dichloropyridine-3-sulfonyl Chloride

Produkt 1

HCID 646088045,6-dichloro-N-[3-(dimethylamino)propyl]-N-methylpyridine-3-sulfonamideAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

With cooling with ice, triethylamine (0.57 ml, 4.06 mmol) and N,N,N′-trimethylpropane-1,3-diamine (0.34 ml, 2.23 mmol) were added to a tetrahydrofuran solution (5 ml) of 5,6-dichloropyridin-3-sulfonyl chloride (500 mg, 2.03 mmol), and stirred for 5 minutes. Saturated saline water was added to the reaction solution, extracted with chloroform, and the organic layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure. The obtained residue was purified by amine-type silica gel column chromatography (Biotage NH, hexane:ethyl acetate=6:1 to 4:1) to obtain 5,6-dichloro-N-[3-(dimethylamino)propyl]-N-methylpyridine-3-sulfonamide (454 mg, yield: 69%) as a red solid.

Aufarbeitung

  1. extractionextracted with chloroform
  2. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe obtained residue was purified by amine-type silica gel column chromatography (Biotage NH, hexane:ethyl acetate=6:1 to 4:1)

Quellen und Nachweise

ORD-Eintrag
ord-30d413919aa64b44b3d9134595c4c0ad
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846700B2

Verknüpfte Notizen

Wird geladen…