Phosgene → 2-Isocyanatoethyl methacrylate

HRID 1277746

반응식

HRID 1277746 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

HCID 354092-Isocyanatoethyl methacrylate수율 95%

시약·촉매·용매 2

HCID 962Water용매2회HCID 6344Dichloromethane용매2회

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-87b81873d6d64583befc2d3613b520ed
출처 데이터셋
uspto-grants-1981_07
특허 번호
US04278809

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