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

HRID 81672Notes

Reaction equation

HRID 81672 reaction equation
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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-30d413919aa64b44b3d9134595c4c0ad
Source dataset
uspto-grants-2014_09
Patent number
US08846700B2

Reaction notes

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