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

HRID 500486Notes

Reaction equation

HRID 500486 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-f98d6ff45d124371959d012aa2c20386
Source dataset
uspto-grants-2010_08
Patent number
US07772229B2

Reaction notes

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