Acetyl chloride → N-[(6-Bromopyridin-2-yl)sulphonyl]acetamide

HRID 2359918Notes

Reaction equation

HRID 2359918 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([S:8]([NH2:11])(=[O:10])=[O:9])[CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[C:18](Cl)(=[O:20])[CH3:19]>C(#N)C>[Br:1][C:2]1[N:7]=[C:6]([S:8]([NH:11][C:18](=[O:20])[CH3:19])(=[O:9])=[O:10])[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 11430Potassium CarbonateHCID 573458166-Bromopyridine-2-sulfonamide

Product 1

HCID 86667250N-[(6-Bromopyridin-2-yl)sulphonyl]acetamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

6-Bromopyridine-2-sulphonamide (0.5 g, 2.11 mmol, prepared by the methods described in WO2005/058299) and potassium carbonate (2.92 g, 21.1 mmol) were initially charged in acetonitrile (10 ml). While cooling with ice, acetyl chloride (1.16 g, 14.8 mmol) was added dropwise and the reaction mixture was stirred at room temperature for 16 h. The solvent was removed under reduced pressure, and the residue was taken up in water and acidified with dilute hydrochloric acid solution. It was extracted with ethyl acetate and the solvent was removed under reduced pressure. This gave 0.54 g (85% of theory) of N-[(6-bromopyridin-2-yl)sulphonyl]-acetamide.

Workup

  1. additionwas added dropwise
  2. customThe solvent was removed under reduced pressure
  3. extractionIt was extracted with ethyl acetate
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-e4177b39fa5f40ca9af2143ba7806818
Source dataset
uspto-grants-2014_04
Patent number
US08686004B2

Reaction notes

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