Sodium hydride → HCID 57663184, compound

HRID 548750Notes

Reaction equation

HRID 548750 reaction equation
[H-].[Na+].F[C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1[S:11]([NH:14][CH2:15][CH2:16][OH:17])(=[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])[NH:14][CH2:15][CH2:16][O:17][C:6]=2[CH:7]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 43501950HCID 43501950, compound

Product 1

HCID 57663184HCID 57663184, compoundYield 28.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% dispersion in mineral oil) (260 mg, 6.49 mmol) was added to a solution of 2,4-difluoro-N-(2-hydroxyethyl)benzenesulfonamide (0.7 g, 2.95 mmol) in DMF (100 mL) and the mixture stirred at RT for 48 hours. The solvent was removed in vacuo, iced water (200 mL) added and the mixture extracted into ethyl acetate. The combined organic extracts were washed with brine (40 mL), dried (MgSO4), filtered and reduced in vacuo to give a white solid which was chromatographed on silica, eluting with 20-70% ethyl acetate in isohexane, to give the desired compound as a white solid (0.18 g). 1H NMR δ (CDCl3): 3.65-3.70 (m, 2H), 4.25-4.27 (m, 2H), 4.69 (t, 1H), 6.86-6.94 (m, 2H), 7.82-7.86 (m, 1H); m/z 216 (M−H)−

Workup

  1. customThe solvent was removed in vacuo, iced water (200 mL)
  2. additionadded
  3. extractionthe mixture extracted into ethyl acetate
  4. washThe combined organic extracts were washed with brine (40 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customto give a white solid which
  8. customwas chromatographed on silica
  9. washeluting with 20-70% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-3f1f031157d941728efe102e78b831f7
Source dataset
uspto-grants-2011_05
Patent number
US07943607B2

Reaction notes

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