Methyl iodide → HCID 23346529, compound

HRID 1856252Notes

Reaction equation

HRID 1856252 reaction equation
[C:1]1([CH3:15])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[NH:9][S:10]([CH:13]=[CH2:14])(=[O:12])=[O:11].[C:16](=O)([O-])[O-].[Na+].[Na+].CI>CC(C)=O>[C:1]1([CH3:15])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[N:9]([CH3:16])[S:10]([CH:13]=[CH2:14])(=[O:12])=[O:11]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10340Sodium CarbonateHCID 23346511HCID 23346511, compound

Product 1

HCID 23346529HCID 23346529, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

22.5 g (0.1 mole) N-mesitylethenesulphonamide, 37.2 g anhydrous sodium carbonate, 52 ml methyl iodide and 1000 ml acetone were mixed and refluxed for 6 hours. The mixture was then filtered and evaporated to dryness. The residue was dissolved in diethyl ether and extracted with 2 N sodium hydroxide solution (to remove remaining starting material). The ether solution was dried over magnesium sulphate and evaporated to dryness. 24.0 g of the crude title compound was obtained as an oil, which solidifies slowly. M.p. c.a. 25° C.

Workup

  1. temperaturerefluxed for 6 hours
  2. filtrationThe mixture was then filtered
  3. customevaporated to dryness
  4. dissolutionThe residue was dissolved in diethyl ether
  5. extractionextracted with 2 N sodium hydroxide solution (to remove remaining starting material)
  6. dry with materialThe ether solution was dried over magnesium sulphate
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-0c1548d98e57493384e82736b58dd97f
Source dataset
uspto-grants-1980_08
Patent number
US04218476

Reaction notes

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