Methanesulfonyl chloride → N-(6-Chloro-2-methylpyridin-3-yl)methanesulfonamide

HRID 607499Notes

Reaction equation

HRID 607499 reaction equation
[NH2:1][C:2]1[C:3]([CH3:9])=[N:4][C:5]([Cl:8])=[CH:6][CH:7]=1.[CH3:10][S:11](Cl)(=[O:13])=[O:12]>N1C=CC=CC=1>[Cl:8][C:5]1[N:4]=[C:3]([CH3:9])[C:2]([NH:1][S:11]([CH3:10])(=[O:13])=[O:12])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 70095003-Amino-6-chloro-2-picoline

Product 1

HCID 86639047N-(6-Chloro-2-methylpyridin-3-yl)methanesulfonamideYield 55%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 3-amino-6-chloro-2-picoline (2.0 g, 14.0 mmol) and methanesulfonyl chloride (1.92 g, 16.8 mmol) in pyridine (40 ml) was stirred for 1 hour at room temperature. After removal of the solvent, the resulting crude product was purified by silica gel column chromatography, eluting with hexane/EtOAc (3:2), to afford 1.70 g (55% yield) of the title compound as pale yellow solids.

Workup

  1. customAfter removal of the solvent
  2. customthe resulting crude product was purified by silica gel column chromatography
  3. washeluting with hexane/EtOAc (3:2)

Sources & evidence

ORD record
ord-e57ca3b885464a7b80895b7a70d8629d
Source dataset
uspto-grants-2011_03
Patent number
US07915448B2

Reaction notes

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