Acetonitrile → N,N-bis(2-oxiranylmethyl)benzenesulfonamide

HRID 411151Notes

Reaction equation

HRID 411151 reaction equation
[C:1](#[N:3])[CH3:2].[CH2:4]([CH:6]1[O:8][CH2:7]1)Cl.[C:9]1([S:15](N)(=[O:17])=[O:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[C:19](=O)([O-])[O-:20].[Cs+].[Cs+]>O>[O:20]1[CH2:19][CH:2]1[CH2:1][N:3]([CH2:4][CH:6]1[CH2:7][O:8]1)[S:15]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:17])=[O:16]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 7370BenzenesulfonamideHCID 7835EpichlorohydrinHCID 10796Cesium carbonate

Product 1

HCID 11207928N,N-bis(2-oxiranylmethyl)benzenesulfonamideYield 46%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

This reaction is very exothermic so care must be taken if the reaction is scaled up. Acetonitrile (400 mL) and (+)-epichlorohydrin (100 mL, 118.3 g, 0.78 mol) were added to benzenesulfonamide (50.0 g, 0.32 mol), followed by cesium carbonate (228 g, 0.70 mol). The mixture was heated at reflux for 15 hours with mechanical stirring. After cooling to room temperature water was added (250 mL) and the organic phase separated and concentrated under reduced pressure. The residual oil was chromatographed over silica (300 g), eluting with dichloromethane (1 L) and then dichloromethane:ethyl acetate (3 L of 19:1), to give the sub-title compound as an oil (39.4 g, 46%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 15 hours with mechanical stirring
  3. additionwas added (250 mL)
  4. customthe organic phase separated
  5. concentrationconcentrated under reduced pressure
  6. customThe residual oil was chromatographed over silica (300 g)
  7. washeluting with dichloromethane (1 L)

Sources & evidence

ORD record
ord-563fd8b4fec64110b58832c1090ee993
Source dataset
uspto-grants-2003_05
Patent number
US06559143B1

Reaction notes

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