Sodium hydride → 2,3-Dichloro-4-fluoro-N-(3-methoxy-2-pyrazinyl)benzenesulphonamide

HRID 1444082Notes

Reaction equation

HRID 1444082 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[C:6]([NH2:11])=[N:7][CH:8]=[CH:9][N:10]=1.[Cl:12][C:13]1[C:18]([Cl:19])=[C:17]([F:20])[CH:16]=[CH:15][C:14]=1[S:21](Cl)(=[O:23])=[O:22]>CN1CCCC1=O>[Cl:12][C:13]1[C:18]([Cl:19])=[C:17]([F:20])[CH:16]=[CH:15][C:14]=1[S:21]([NH:11][C:6]1[C:5]([O:4][CH3:3])=[N:10][CH:9]=[CH:8][N:7]=1)(=[O:23])=[O:22]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 124898513-Methoxypyrazin-2-amineHCID 591682102,3-Dichloro-4-fluorobenzenesulphonyl chloride

Product 1

HCID 101936292,3-Dichloro-4-fluoro-N-(3-methoxy-2-pyrazinyl)benzenesulphonamide

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Sodium hydride (0.4 g of a 60% dispersion in oil) was added to a solution of 3-methoxy-2-pyrazinamine (0.25 g) in N-methylpyrrolidinone (10 mL). After 0.5 h, 2,3-dichloro-4-fluorobenzenesulphonyl chloride (Example 185a) (0.63 g) was added. After 16 h at room temperature the reaction mixture was quenched with 2M aqueous HCl, extracted with ethyl acetate, dried (MgSO4) and evaporated. Purification was by silica gel chromatography eluting with ethyl acetate/iso-hexane mixtures. Yield 0.16 g.

Workup

  1. customAfter 16 h at room temperature the reaction mixture was quenched with 2M aqueous HCl
  2. extractionextracted with ethyl acetate
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customPurification
  6. washeluting with ethyl acetate/iso-hexane mixtures

Sources & evidence

ORD record
ord-8b215d31b841497fba13b7f6408a03b3
Source dataset
uspto-grants-2010_02
Patent number
US07662825B2

Reaction notes

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