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

HRID 1822942Notes

Reaction equation

HRID 1822942 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-559b72fe2a0c46848428a622716a1279
Source dataset
uspto-grants-2006_05
Patent number
US07037927B2

Reaction notes

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