1,1-Dichloroethane → Methacryloyl isocyanate

HRID 622229Notes

Reaction equation

HRID 622229 reaction equation
Cl.[C:2]([C:5]1[O:6]C(=O)[C:8](=[O:10])[N:9]=1)([CH3:4])=[CH2:3].[Cl:12]C(Cl)C>O>[C:5]([N:9]=[C:8]=[O:10])(=[O:6])[C:2]([CH3:4])=[CH2:3].[CH3:3][CH:2]([CH2:4][Cl:12])[C:5]([N:9]=[C:8]=[O:10])=[O:6]

Participants

5

Reactant 2

HCID 63651,1-DichloroethaneHCID 221576152-Isopropenyloxazoline-4,5-dione hydrochloride

Product 2

HCID 10942374Methacryloyl isocyanateHCID 137662253-Chloro-2-methylpropanoyl isocyanate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 2-isopropenyloxazoline-4,5-dione hydrochloride (200 g; 1.14 mol), dichloroethane (800 g) was added, and the resultant mixture was heated to 60°-65° C. while stirring for about 5.5 hours. After cooling with water, the reaction mixture was distilled under reduced pressure to give methacryloyl isocyanate (25.3 g) and alpha-methyl-beta-chloropropionyl isocyanate (80.7 g).

Workup

  1. distillationthe reaction mixture was distilled under reduced pressure

Sources & evidence

ORD record
ord-e7bfa278d6ff41eda86bfec879657088
Source dataset
uspto-grants-1988_09
Patent number
US04769485

Reaction notes

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