Sodium hydride → 7-fluoro-2-methyl-3,4-dihydro-2H-5,1,2-benzoxathiazepine 1,1-dioxide

HRID 548746Notes

Reaction equation

HRID 548746 reaction equation
[H-].[Na+].F[C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1[S:11]([N:14]([CH2:16][CH2:17][OH:18])[CH3:15])(=[O:13])=[O:12]>CN(C=O)C>[F:10][C:8]1[CH:9]=[CH:4][C:5]2[S:11](=[O:13])(=[O:12])[N:14]([CH3:15])[CH2:16][CH2:17][O:18][C:6]=2[CH:7]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 576631632,4-difluoro-N-(2-hydroxyethyl)-N-methylbenzenesulfonamide

Product 1

HCID 576631787-fluoro-2-methyl-3,4-dihydro-2H-5,1,2-benzoxathiazepine 1,1-dioxideYield 58.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% dispersion in mineral oil) (700 mg, 17.51 mmol) was added to a solution of 2,4-difluoro-N-(2-hydroxyethyl)-N-methylbenzenesulfonamide (2 g, 7.96 mmol) in DMF (200 mL) and the mixture stirred at RT for 48 hours. The solvent removed in vacuo, iced water (200 mL) added and the mixture extracted into ethyl acetate. The combined organic extract was washed with brine (40 mL), dried (MgSO4), filtered and reduced in vacuo to give a white solid which was chromatographed on silica, eluting with 20-50% ethyl acetate in isohexane, to give the desired compound as a white solid (1.08 g).

Workup

  1. customThe solvent removed in vacuo, iced water (200 mL)
  2. additionadded
  3. extractionthe mixture extracted into ethyl acetate
  4. extractionThe combined organic extract
  5. washwas washed with brine (40 mL)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customto give a white solid which
  9. customwas chromatographed on silica
  10. washeluting with 20-50% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-a4c1aa5ecf144371b19fe76a49ec5985
Source dataset
uspto-grants-2011_05
Patent number
US07943607B2

Reaction notes

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