77066-66-1Relevant articles and documents
Orthoamides, XXXVII. Reactions of 2,2-Bis(dialkylamino)acetonitriles and 2-(Dialkylamino)-2-methoxyacetonitriles with Isocyanates
Kantlehner, Willi,Haug, Erwin,Isak, Heinz,Schulz, Wolfgang,Hippich, Silvin,et al.
, p. 1721 - 1732 (2007/10/02)
The nitriles 1a - c react with isocyanates to give the parabanic acid aminals 10a - g.By alcoholysis of the aminals 10 the parabanic acid O,N-acetals 12a - d are prepared.Compounds of type 12 are also accessible from the amide acetal 3a and 5-imino-2,4-imidazolidinediones 13.By means of the 14C-labelled nitrile 22 it is shown that the C-5 atom of the imidazolidine system in 10 arises from the nitrile group of 1.Hence, the reactions yielding the compounds 10 are mechanistically not related with the reactions of the amide acetals 3 with isocyanates giving parabanic acid O,N-acetals 7.From the complex product mixtures, formed in the reaction of the nitriles 2 with isocyanates, the parabanic acid O,N-acetals 7a - c and the 5-imino-2,4-imidazolidinediones 13a,c are isolated.