Divinyl sulfone → 4-Benzylthiomorpholine 1,1-Dioxide

HRID 433949Notes

Reaction equation

HRID 433949 reaction equation
[CH:1]([S:3]([CH:6]=[CH2:7])(=[O:5])=[O:4])=[CH2:2].[CH2:8]([NH2:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C(O)C>[CH2:8]([N:15]1[CH2:7][CH2:6][S:3](=[O:5])(=[O:4])[CH2:1][CH2:2]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 6496Divinyl sulfoneHCID 7504Benzylamine

Product 1

HCID 3184544-Benzylthiomorpholine 1,1-DioxideYield 39.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Divinyl sulphone (0.8 ml, 10 mmol) was added to a solution of benzylamine (1.09 ml, 10 mmol) in ethanol (4 ml) and heated under reflux for 2 hours. The solvent was removed under reduced pressure, the residue dissolved in dichloromethane (30 ml) and washed with saturated aqueous sodium hydrogencarbonate solution (15 ml), dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel eluting with a gradient system of dichloromethane:methanol (100:0 to 99:1) to afford the title compound as a yellow oil (0.9 g).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 2 hours
  3. customThe solvent was removed under reduced pressure
  4. dissolutionthe residue dissolved in dichloromethane (30 ml)
  5. washwashed with saturated aqueous sodium hydrogencarbonate solution (15 ml)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by column chromatography on silica gel eluting with a gradient system of dichloromethane:methanol (100:0 to 99:1)

Sources & evidence

ORD record
ord-1b06437c69b447bea9aea42d002cdbf0
Source dataset
uspto-grants-2003_12
Patent number
US06670366B1

Reaction notes

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