Sodium hydride → HCID 66223428, compound

HRID 2364361Notes

Reaction equation

HRID 2364361 reaction equation
[H-].[Na+].[CH3:3][O:4][CH:5]([O:15][CH3:16])[CH2:6][NH:7][S:8]([CH2:11][CH2:12][CH2:13]Cl)(=[O:10])=[O:9]>CN(C)C=O>[CH3:3][O:4][CH:5]([O:15][CH3:16])[CH2:6][N:7]1[CH2:13][CH2:12][CH2:11][S:8]1(=[O:10])=[O:9]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 61248038HCID 61248038, compound

Product 1

HCID 66223428HCID 66223428, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a cold (0° C.) suspension of sodium hydride (267 mg, 60% in oil, 6.67 mmol) in N,N-dimethylformamide (30 mL) was added N-[2,2-bis(methyloxy)ethyl]-3-chloro-1-propanesulfonamide (1.49 g, 6.06 mmol) in N,N-dimethylformamide (10 mL) dropwise. The reaction mixture was warmed to room temperature and stirred one hour. The reaction mixture was poured onto ice and extracted with toluene. The organic layer was washed with water and brine, then dried over sodium sulfate. Filtration and concentration provided 2-[2,2-bis(methyloxy)ethyl]isothiazolidine 1,1-dioxide as a clear oil. 1H NMR (400 MHz, CDCl3) δ 4.51 (t, J=5.3 Hz, 1 H), 3.41-3.37 (m, 8 H), 3.17-3.11 (m, 4 H), 2.35 (m, 2 H).

Workup

  1. additionThe reaction mixture was poured onto ice
  2. extractionextracted with toluene
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-d01ad8ff06d44952a8c087e1aecd2592
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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