Acrylonitrile → HCID 18976536, compound

HRID 2393668Notes

Reaction equation

HRID 2393668 reaction equation
[CH3:1][N:2]1[CH2:8][C:6](=O)[NH:5][C:3]1=[O:4].[C:9](#[N:12])[CH:10]=[CH2:11].[OH-:13].[Na+]>Cl>[CH3:1][N:2]1[C:8](=[O:13])[CH2:6][N:5]([CH2:11][CH2:10][C:9]#[N:12])[C:3]1=[O:4]

Participants

5

Reactant 3

HCID 7855AcrylonitrileHCID 14798Sodium HydroxideHCID 692171-Methylhydantoin

Product 1

HCID 18976536HCID 18976536, compoundYield 74.3%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidCatalyst

Procedure

87.0 g (0.762 mol) of 1-methylhydantoin and 48.55 g (0.915 mol) of acrylonitrile are introduced into an apparatus at an internal temperature of 67° C., and 8 ml of 1 molar sodium hydroxide solution are added dropwise over the course of 12 minutes, during which an exothermic reaction occurs and the temperature rises to 75° C. The reaction mixture is then stirred for 1 hour and 48 minutes at 75° C.-103° C. and then neutralized with 0.92 g of 32% hydrochloric acid. The reaction product is purified by vacuum distillation, giving 94.7 g (74.3% of theory) of crystalline 3-(3-methyl-2,4-dioxoimidazolidin-1-yl)propionitrile, whose melting point is 53° C.

Workup

  1. additionare added dropwise over the course of 12 minutes, during which
  2. customan exothermic reaction
  3. customrises to 75° C
  4. distillationThe reaction product is purified by vacuum distillation

Sources & evidence

ORD record
ord-611db583a7574e80bb55ce3dd0de5a67
Source dataset
uspto-grants-1998_09
Patent number
US05807927

Reaction notes

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