Acrylonitrile → HCID 606527, compound

HRID 972456Notes

Reaction equation

HRID 972456 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]1[C:11]([CH3:13])([CH3:12])[C:9](=[O:10])[N:8]([CH2:14][CH2:15][CH2:16][NH2:17])[C:6]1=[O:7].C(#N)C=C>>[C:2]([CH2:3][CH2:4][N:5]1[C:11]([CH3:12])([CH3:13])[C:9](=[O:10])[N:8]([CH2:14][CH2:15][C:16]#[N:17])[C:6]1=[O:7])#[N:1]

Participants

3

Reactant 2

HCID 7855AcrylonitrileHCID 30152731,3-Bis(3-aminopropyl)-5,5-dimethylimidazolidine-2,4-dione

Product 1

HCID 606527HCID 606527, compound

Procedure

A diamine containing the hydantoin ring is 1,3-bis-(3-aminopropyl)-5,5-dimethylhydantoin which may be prepared as described by Sato, Nippon Kaguku Zasshi, 83, 318-23 (1962). 5-5-dimethylhydantoin is reacted with acrylonitrile yielding 1,3-bis (2-cyanoethyl)-5,5-dimethylhydantoin which is further reacted with hydrogen gas in the presence of Raney nickel to yield 1,3-bis-(3-aminopropyl)-5,5-dimethylhydantoin. This compound is available semi-commercially from Glyco, Inc. as Dantomin DAP.

Workup

  1. custommay be prepared

Sources & evidence

ORD record
ord-889eb6e29ecc48529780a0d2be26db90
Source dataset
uspto-grants-1977_10
Patent number
US04053441

Reaction notes

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