Or maybe phenylacetonisonitrile ?
Does or can this chemical exist ?
Could it be made like this :
C6H5CH2NH2 + CHCl3 + 3KOH = C6H5CH2NC + 3KCl + 3H2O
John Lennon - Working Class Hero
Yes, isonitriles exist. They are undesired byproducts in the synthesis from benzylchloride and alkali cyanide. You can destroy the isonitriles with concentrated sulphuric acid. See the "organic syntheses" for a detailed recipe. Isonitrile has a very unpleasant smell.
I know that isonitriles rearrange themselves to nitriles if heated.
I was thinking of using this as a path to benzyl cyanide from benzylamine.
Toluene/Benzyl Alcohol > Benzyl Chloride > Benzylamine > Benzyl Isocyanide > Benzyl Cyanide > Phenylacetic Acid
John Lennon - Working Class Hero
You'll have to experiment with it to find out for sure if that method will work, but a very clever idea.
Can this be done to an aniline? Ph-NH2 --> Ph-N#C (# = triple bond)
That would be great! Or one could turn a benzylamine of your choosing into the phenethylamine of your choosing by
PhCH2-NH2 --> PhCH2-N#C --> PhCH2-C#N --> PhCH2CH2-NH2 (via reduction)
hmm, 2,5-dimethoxy-N-methyl-aniline --> 2,5-dimethoxy-4-methyl-aniline, and from there to 2CD. :)
PrimoPyro
I am really struggling to find any details on the rearangement of isonitriles to nitriles (isocyanides to cyanides). I have done extensive patent searching with no results and also comprehensive engine searches with no luck.
All I have is a small passage in an organic chemistry book saying that, on heating isonitriles undergo rearrangement, forming nitriles.
Another interesting thing I found :
A newer method of synthesizing nitriles is to pass the vapour of the carboxylic acid or its ester, mixed with ammonia, over heated alumina at 500°c.
John Lennon - Working Class Hero
Try heating the isonitriles in a high boiling suitable solvent (water free, and non-reactive with the isonitrile or the product) at temps around 180-220*C for a couple of hours then test however you can.