Phosgene → 2-Isocyanatoethyl methacrylate

HRID 1277746Notes

Reaction equation

HRID 1277746 reaction equation
[C:1]([C:4]1[O:5][CH2:6][CH2:7][N:8]=1)([CH3:3])=[CH2:2].[C:9](Cl)(Cl)=[O:10].[OH-:13].[Na+]>O.C(Cl)Cl>[C:4]([O:5][CH2:6][CH2:7][N:8]=[C:9]=[O:10])(=[O:13])[C:1]([CH3:3])=[CH2:2]

Participants

6

Reactant 3

HCID 6371PhosgeneHCID 14798Sodium HydroxideHCID 826512-Isopropenyl-2-oxazoline

Product 1

HCID 354092-Isocyanatoethyl methacrylateYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A 3-liter jacketed reactor vessel was charged with 100 ml of methylene chloride and cooled to approximately 0° C. A solution of 2-isopropenyl-2-oxazoline (100 g) in 177 ml of water, a solution of phosgene (131.5 g) in 400 ml of methylene chloride, and a solution of 35 weight percent sodium hydroxide in water were added simultaneously to the reaction vessel with stirring and cooling. The rates of addition were such that the three reagents were added over approximately a 50 minute time span with the temperature being maintained at 10° to 18° C. Stirring was continued for two minutes and the layers allowed to separate. The organic layer was washed twice with 100 ml portions of a saturated aqueous sodium bicarbonate solution, dried over sodium sulfate and concentrated under reduced pressure. The colorless concentrate was inhibited with 0.1 g of phenothiazine and the desired product recovered therefrom as a colorless liquid (133.6 g) boiling at 46°-47° C./0.4 mm Hg. Product yield 95-96 percent of theory.

Workup

  1. temperaturecooling
  2. additionThe rates of addition
  3. additionwere added over approximately a 50 minute time span with the temperature
  4. temperaturebeing maintained at 10° to 18° C
  5. stirringStirring
  6. customto separate
  7. washThe organic layer was washed twice with 100 ml portions of a saturated aqueous sodium bicarbonate solution
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. concentrationThe colorless concentrate
  11. customthe desired product recovered

Sources & evidence

ORD record
ord-87b81873d6d64583befc2d3613b520ed
Source dataset
uspto-grants-1981_07
Patent number
US04278809

Reaction notes

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