Dimethylamine → 2-chloro-N,N-dimethyl-3-pyridinesulfonamide

HRID 736398Notes

Reaction equation

HRID 736398 reaction equation
[Cl:1][C:2]1[C:7]([S:8](Cl)(=[O:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:12][NH:13][CH3:14]>C1COCC1>[Cl:1][C:2]1[C:7]([S:8]([N:13]([CH3:14])[CH3:12])(=[O:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 102199682-Chloropyridine-3-sulfonyl chloride

Product 1

HCID 122039042-chloro-N,N-dimethyl-3-pyridinesulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2-Chloro-3-pyridinesulfonyl chloride in THF (10 mL) was treated with a 2.0M solution of dimethylamine in THF (8 mL, 16 mmol). After stirring for 10 hours, the mixture was quenched with saturated aqueous NH4Cl and extracted with ethyl acetate. The organics were concentrated under reduced pressure and the residue was purified by flash chromatography (30% ethyl acetate in hexanes) to provide the title compound.

Workup

  1. customthe mixture was quenched with saturated aqueous NH4Cl
  2. extractionextracted with ethyl acetate
  3. concentrationThe organics were concentrated under reduced pressure
  4. customthe residue was purified by flash chromatography (30% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-af4593d66c7740478457afa51ce1f6a9
Source dataset
uspto-grants-2009_09
Patent number
US07595332B2

Reaction notes

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