Acrylamide → 2-Vinyloxazoline-4,5-dione hydrochloride

HRID 979264

Reaction equation

HRID 979264 reaction equation
[C:1](Cl)(=[O:5])[C:2]([Cl:4])=[O:3].[C:7]([NH2:11])(=[O:10])[CH:8]=[CH2:9]>ClC(Cl)C>[ClH:4].[CH:8]([C:7]1[O:10][C:1](=[O:5])[C:2](=[O:3])[N:11]=1)=[CH2:9]

Participants

4

Reactant 2

HCID 6579AcrylamideHCID 65578Oxalyl chloride

Product 1

HCID 212839312-Vinyloxazoline-4,5-dione hydrochlorideYield 99.7%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

Oxalyl chloride (130 g; 1.02 mol) was charged in a reactor, and a warm solution of acrylamide (71 g; 1.0 mol) in dichloroethane (250 ml) was dropwise added thereto (reaction temperature, 10° to 30° C.). After completion of the dropwise addition, the solvent and excess of the oxalyl chloride were removed by distillation under reduced pressure to obtain 2-vinyloxazoline-4,5-dione hydrochloride (161 g) as a yellow oil. Viscosity, 100,000 cp.

Workup

  1. custom(reaction temperature, 10° to 30° C.)
  2. additionAfter completion of the dropwise addition
  3. customthe solvent and excess of the oxalyl chloride were removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-ab210d8767f44196a46aaad63d336125
Source dataset
uspto-grants-1987_05
Patent number
US04666993

Linked notes

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