Tetrahydrofuran → 5,6-dichloro-N-[2-(dimethylamino)ethyl]-N-methylpyridine-3-sulfonamide

HRID 1517309Notes

Reaction equation

HRID 1517309 reaction equation
C(N(CC)CC)C.[CH3:8][N:9]([CH3:14])[CH2:10][CH2:11][NH:12][CH3:13].O1CCCC1.[Cl:20][C:21]1[CH:22]=[C:23]([S:28](Cl)(=[O:30])=[O:29])[CH:24]=[N:25][C:26]=1[Cl:27]>O>[Cl:20][C:21]1[CH:22]=[C:23]([S:28]([N:12]([CH2:11][CH2:10][N:9]([CH3:14])[CH3:8])[CH3:13])(=[O:30])=[O:29])[CH:24]=[N:25][C:26]=1[Cl:27]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 673381,2-Ethanediamine, N1,N1,N2-trimethyl-HCID 47369115,6-dichloropyridine-3-sulfonyl Chloride

Product 1

HCID 646088035,6-dichloro-N-[2-(dimethylamino)ethyl]-N-methylpyridine-3-sulfonamideYield 73%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

With cooling with ice, triethylamine (0.57 ml, 4.06 mmol) and N,N,N′-trimethylethane-1,2-diamine (0.30 ml, 2.23 mmol) were added to a tetrahydrofuran solution (5 ml) of 5,6-dichloropyridine-3-sulfonyl chloride (500 mg, 2.03 mmol) obtained in the above reaction, and stirred for 5 minutes. Saturated saline water was added to the reaction solution, extracted with chloroform, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by amine-type silica gel column chromatography (Biotage NH, hexane:ethyl acetate=5:1 to 3:1) to obtain 5,6-dichloro-N-[2-(dimethylamino)ethyl]-N-methylpyridine-3-sulfonamide (460 mg, yield: 73%) as a red solid.

Workup

  1. customobtained in the above reaction
  2. extractionextracted with chloroform
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by amine-type silica gel column chromatography (Biotage NH, hexane:ethyl acetate=5:1 to 3:1)

Sources & evidence

ORD record
ord-01b3d009cc6d4dee841f525bd4a4331d
Source dataset
uspto-grants-2012_07
Patent number
US08232284B2

Reaction notes

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