Ethyl Bromide → HCID 822845, compound

HRID 1489538Notes

Reaction equation

HRID 1489538 reaction equation
[C:1]1([NH:7][S:8]([CH3:11])(=[O:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])([O-])=O.[K+].[K+].[CH2:18](Br)[CH3:19]>>[CH2:18]([N:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[S:8]([CH3:11])(=[O:10])=[O:9])[CH3:19]

Participants

4

Reactant 3

HCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 70970Methanesulfonamide, N-phenyl-

Product 1

HCID 822845HCID 822845, compoundYield 92%

Conditions

Temperature
0 °C

Procedure

16.7 g(100 mmol) of N-phenylmethanesulfonamide and 27.6 g (212 mmol) of K2CO3 were dissolved in 200 ml of dimethylform-amide(DMF) and the resulting solution was cooled to 0° C. 11.7 g(110 mmol) of ethylbromide was added dropwise thereto, which was stirred for over 10 hours at room temperature. DMF was distilled off under a reduced pressure and the residue was dissolved in dichloromethane. The resulting solution was washed with water and the organic layer was dried over anhydrous MgSO4. The organic solvent was distilled off under a reduced pressure to obtain 17.9 g of the title compound(yield 92%).

Workup

  1. distillationDMF was distilled off under a reduced pressure
  2. dissolutionthe residue was dissolved in dichloromethane
  3. washThe resulting solution was washed with water
  4. dry with materialthe organic layer was dried over anhydrous MgSO4
  5. distillationThe organic solvent was distilled off under a reduced pressure

Sources & evidence

ORD record
ord-15ac76203c2e4ae89f729119cbd4fb65
Source dataset
uspto-grants-1997_10
Patent number
US05679687

Reaction notes

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