Sodium hydride → HCID 21910631, compound

HRID 1245287Notes

Reaction equation

HRID 1245287 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][S:9]([NH:12][C:13]([CH3:18])([CH3:17])[C:14](=O)[CH3:15])(=[O:11])=[O:10])=[CH:4][CH:3]=1.[H-].[Na+]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][S:9]([NH:12][C:13]([CH3:18])([CH3:17])[C:14]#[CH:15])(=[O:11])=[O:10])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 21910638HCID 21910638, compound

Product 1

HCID 21910631HCID 21910631, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution-of C-(4-Chloro-phenyl)-N-(1,1-dimethyl-2-oxo-propyl)-methanesulfonamide, 4.2 g (15.0 mmol) in 60 mL of dimethylformamide was added 1.3 g (31.5 mmol) of sodium hydride. The reaction mixture was heated at 90° C. for 24 H, then cooled to ambient temperature and concentrated to dryness. The residue was partitioned between ethyl acetate and water and was acidified to pH=3.0 with 1 N HCl. The mixture was extracted with ethyl acetate. The combined organics were washed with brine, dried over sodium sulfate, filtered and concentrated to dryness. The residue was chromatographed over silica using chloroform as eluant to yield 3.27 g (80%) of the desired product, shown below, as a tan solid. 1H-NMR is consistent with structure; MS (ion spray) 270.3 (M−1); Anal. Calc'd for C12H14ClNO2S: C, 53.04; H, 5.19; N, 5.15. Found: C, 52.72; H, 5.18; N, 4.98. 5-(4-Chloro-phenyl)-3,3,4-trimethyl-2,3-dihydro-isothiazole 1,1-dioxide.

Workup

  1. temperaturecooled to ambient temperature
  2. concentrationconcentrated to dryness
  3. customThe residue was partitioned between ethyl acetate and water
  4. extractionThe mixture was extracted with ethyl acetate
  5. washThe combined organics were washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness
  9. customThe residue was chromatographed over silica

Sources & evidence

ORD record
ord-a39b55d49ed140f399410512c91ed849
Source dataset
uspto-grants-2006_10
Patent number
US07125840B2

Reaction notes

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