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

HRID 500484Notes

Reaction equation

HRID 500484 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-40f797321bd0451db25fcdaf0e83b71c
Source dataset
uspto-grants-2010_08
Patent number
US07772229B2

Reaction notes

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