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

HRID 411153Notes

Reaction equation

HRID 411153 reaction equation
[C:1](#[N:3])[CH3:2].[CH2:4]([C@@H: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 10796Cesium carbonateHCID 2734062(-)-Epichlorohydrin

Product 1

HCID 11207928N,N-bis(2-oxiranylmethyl)benzenesulfonamideYield 43%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

This reaction is very exothermic so care must be taken if the reaction is scaled up. Acetonitrile (100 mL) and (R)-(−)-epichlorohydrin (47 mL, 55.6 g, 0.60 mol) were added to benzenesulfonamide (20.0 g, 0.127 mol), followed by cesium carbonate (83 g, 0.255 mol). The mixture was heated at reflux for 6 hours with mechanical stirring and then was stirred overnight at room temperature. Water was added (100 mL), the organic phase separated and then concentrated under reduced pressure. The residual oil was chromatographed over silica, eluting with dichloromethane then dichloromethane:ethyl acetate (19:1), to give the sub-title compound as an oil (14.8 g, 43%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 6 hours
  3. stirringwas stirred overnight at room temperature
  4. customthe organic phase separated
  5. concentrationconcentrated under reduced pressure
  6. customThe residual oil was chromatographed over silica
  7. washeluting with dichloromethane

Sources & evidence

ORD record
ord-cc50adcc0545412da8a8dc7662c1e747
Source dataset
uspto-grants-2003_05
Patent number
US06559143B1

Reaction notes

Loading…