2-Vinyloxazoline-4,5-dione hydrochloride → 3-Chloropropanoyl isocyanate

HRID 2232574

Reaction equation

HRID 2232574 reaction equation
[ClH:1].[CH:2]([C:4]1[O:5]C(=O)[C:7](=[O:9])[N:8]=1)=[CH2:3]>ClC1C=CC=CC=1Cl>[C:4]([N:8]=[C:7]=[O:9])(=[O:5])[CH:2]=[CH2:3].[Cl:1][CH2:3][CH2:2][C:4]([N:8]=[C:7]=[O:9])=[O:5]

Participants

4

Reactant 1

HCID 212839312-Vinyloxazoline-4,5-dione hydrochloride

Product 2

HCID 135723743-Chloropropanoyl isocyanateHCID 15597427Acryloyl isocyanate

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

To 2-vinyloxazoline-4,5-dione hydrochloride (100 g), o-dichlorobenzene (400 g) was added, and the resultant mixture was heated at 110° to 120° C. while stirring for about 30 minutes. After cooling with ice, the reaction mixture was distilled under reduced pressure to give acryloyl isocyanate (8.9 g; b.p., 82° to 83° C./760 mmHg) and betachloropropionyl isocyanate (56.4 g).

Workup

  1. temperatureAfter cooling with ice
  2. distillationthe reaction mixture was distilled under reduced pressure

Sources & evidence

ORD record
ord-404a430e477945b2881bef882513fa46
Source dataset
uspto-grants-1988_11
Patent number
US04788256

Linked notes

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