Dimethyl Sulfate → HCID 67797505, compound

HRID 439830Notes

Reaction equation

HRID 439830 reaction equation
[Br:1][CH2:2][C:3]1[CH:4]=[C:5]([CH2:8][NH:9][S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)(=[O:12])=[O:11])[S:6][CH:7]=1.[CH3:19]OS(OC)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:19][N:9]([S:10]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(=[O:11])=[O:12])[CH2:8][C:5]1[S:6][CH:7]=[C:3]([CH2:2][Br:1])[CH:4]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 70346747HCID 70346747, compound

Product 1

HCID 67797505HCID 67797505, compoundYield 15.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 4-bromomethylphenylsulphonyl-2-thienylmethylamine (10.0 g, 28.9 mmol), dimethylsulphate (2.75 ml, 28.9 mmol) and potassium carbonate (19.96 g, 144 mmol) in acetone (100 ml) was stirred overnight at room temperature. The solvent was removed under reduced pressure and the residue taken up in ethyl acetate, washed with water and brine, dried, filtered and evaporated. Chromatography of the residue (1:2 ethyl acetate/hexane) gave N-methyl 4-bromomethylphenylsulphonyl-2-thienylmethylamine (1.60 g, 15%) as a colourless oil which was used directly in the next step.

Workup

  1. customThe solvent was removed under reduced pressure
  2. washwashed with water and brine
  3. customdried
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-312d6d478bf841fb970adfcfd0a08aef
Source dataset
uspto-grants-1996_05
Patent number
US05516783

Reaction notes

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