Dimethyl Sulfate → HCID 53633407, compound

HRID 429511Notes

Reaction equation

HRID 429511 reaction equation
CN(C)[CH:3]=[C:4]([CH2:7][O:8][CH3:9])[CH:5]=[O:6].[OH-].[Na+].S(OC)([O:16][CH3:17])(=O)=O>CO.O>[CH3:17][O:16][CH:3]=[C:4]([CH2:7][O:8][CH3:9])[CH:5]=[O:6]

Participants

6

Reactant 3

HCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 54059009HCID 54059009, compound

Product 1

HCID 53633407HCID 53633407, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 3-(dimethylamino)-2-(methoxymethyl)-2-propenal, (E)- and (Z)- (53.06 g, 0.37 mol) and sodium hydroxide solution (29.7 g, 50, 0.37 mol) in methanol (60 mL) is refluxed for 20 minutes and concentrated in vacuo to obtain a white solid. A solution of the solid in water (250 mL) is treated dropwise with dimethyl sulfate (46.75 g, 0.37 mol), stirred at room temperature for one hour and extracted with methylene chloride. The organic extract is dried over anhydrous sodium sulfate, concentrated in vacuo and distilled to give the title product as a colorless liquid (19.66 g, bp 80° C./0.5 mm Hg, 41% yield).

Workup

  1. concentrationconcentrated in vacuo
  2. customto obtain a white solid
  3. extractionextracted with methylene chloride
  4. extractionThe organic extract
  5. dry with materialis dried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. distillationdistilled

Sources & evidence

ORD record
ord-b5ddb57dd78d400db05980405c2b659b
Source dataset
uspto-grants-2001_11
Patent number
US06316629B1

Reaction notes

Loading…