2-Fluorobenzenesulphonyl chloride → 2-Fluoro-N-(1-methyl-6-oxo-1,6-dihydropyridin-3-yl)benzenesulfonamide

HRID 1772895Notes

Reaction equation

HRID 1772895 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8](Cl)(=[O:10])=[O:9].[NH2:12][C:13]1[CH:14]=[CH:15][C:16](=[O:20])[N:17]([CH3:19])[CH:18]=1>O1CCOCC1.CO>[NH3:12].[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:12][C:13]1[CH:14]=[CH:15][C:16](=[O:20])[N:17]([CH3:19])[CH:18]=1)(=[O:10])=[O:9]

Participants

6

Reactant 2

HCID 1377612-Fluorobenzenesulphonyl chlorideHCID 102200055-Amino-1-methyl-1,2-dihydropyridin-2-one

Product 2

HCID 222AmmoniaHCID 472988402-Fluoro-N-(1-methyl-6-oxo-1,6-dihydropyridin-3-yl)benzenesulfonamideYield 82.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

2-Fluorobenzenesulfonyl chloride (0.46 mL, 3.5 mmol) was added to a solution of 5-amino-1-methyl-1,2-dihydropyridin-2-one (478 mg, 3.85 mmol) in 1,4-dioxane (10 mL) and stirred for 28 h at rt. After concentration in vacuo purification by column chromatography eluting with DCM:MeOH:7M NH3 in MeOH (90:5:5) yielded the title compound (448 mg, 1.59 mmol).

Workup

  1. concentrationAfter concentration
  2. customin vacuo purification by column chromatography
  3. washeluting with DCM

Sources & evidence

ORD record
ord-fab72010499b416091a1aafb64c5aa9b
Source dataset
uspto-grants-2016_02
Patent number
US09249160B2

Reaction notes

Loading…