Phosgene → 14568-37-7

HRID 1277745Notes

Reaction equation

HRID 1277745 reaction equation
[CH3:1][C:2]1[O:3][CH2:4][CH2:5][N:6]=1.[C:7](Cl)(Cl)=[O:8].[OH-:11].[Na+]>O.C(Cl)Cl>[C:2]([O:3][CH2:4][CH2:5][N:6]=[C:7]=[O:8])(=[O:11])[CH3:1]

Participants

6

Reactant 3

HCID 6371PhosgeneHCID 14798Sodium HydroxideHCID 707132-Methyl-2-oxazoline

Product 1

HCID 1313508014568-37-7

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

In like manner, a 3-liter jacketed reaction vessel was charged with 288 ml of methylene chloride and cooled to 0° C. A solution of 2-methyl-2-oxazoline (77.5 g) in 137.7 ml of water, a solution of phosgene (131 g) in 280 ml of methylene chloride, and 250 ml of a 35 weight percent solution of aqueous sodium hydroxide were added simultaneously to the reaction vessel with cooling and stirring; the total additive time was approximately 55 minutes. Stirring was continued for 2 minutes after the addition was complete and the organic and aqueous layers then allowed to separate. The organic layer was isolated and dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The desired product was then obtained from the concentrated organic layer by distillation at 55°/5 mm Hg to give 74.8 g (65 percent of theory) of the desired product as a clear, colorless liquid. The product structure was likewise confirmed by infrared and nuclear magnetic resonance spectroscopy.

Workup

  1. customreaction vessel
  2. temperaturewith cooling
  3. stirringStirring
  4. waitwas continued for 2 minutes
  5. additionafter the addition
  6. customto separate
  7. customThe organic layer was isolated
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-509ed78033db42eea37174f8125777e2
Source dataset
uspto-grants-1981_07
Patent number
US04278809

Reaction notes

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