testimento
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Foul smellers: tert-Butyl isocyanide?
Does anyone have the synthesis of this substance? On itself the molecule doesn't look complex, but the synthesis seems to be. Wiki cites one route
from butylamine:
Me3CNH2 + CHCl3 + 3 NaOH → Me3CNC + 3 NaCl + 3 H2O
This synthesis contains two problematics. One is the benzyltriethylammonium chloride, and the second is, tert-butylamine. Could the PTC be replaced
with something else, and are there any feasible routes for t-butylamine, for ex. from butyl rubber?
On the topic, what are the nastiest (isocyanides) in terms of malodor?
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BromicAcid
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Make your t-butylamine into an N-substitued formamide, dehydrate with phosphorous oxychloride or phosgene in the presence of triethylamine (TEA).
Me<sub>3</sub>CNHC(O)H + COCl<sub>2</sub> ----> Me<sub>3</sub>CNC + CO<sub>2</sub> + 2 HCl (Mopped
up by TEA)
Of course who wants to work with phosgene or phosphorus oxychloride? I have heard of the chloroform method several times and that it is acceptable
for lab-scale preparations. I am sure you could experiment with different phase transfer catalysts that you have more available that may help your
cause. Sometimes the development is half the fun.
As for the stench... I have posted several times on this forum about the stench of these creatures (having made most of the simple isonitriles at the
kilo scale). It's bad... really really bad.... and when it stops being bad, then it's even worse for those around you. Sometimes the smell will
linger on your clothes for days. Early work on many of these compounds was abandoned on the basis of odor alone, and that was back when people were
not deterred very easily. If you are making quantities of this, cover your skin, cover your nose. Suit up so you can remove the suit and not bring
the stink with you. Quench with hydrochloric acid / methanol solution. Drink orange juice to get rid of the taste in the back of your throat.
The "Things I Will Not Work With" blog lists butyl isocyanide as the nastiest of the bunch. It's horrible but at that level.... it's a crap shoot.
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testimento
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Aww, that one seems to turn out really nasty route. A bunch of impossible-to-get chemicals, or then 10 steps from OTC stuff. Yeah, I've got to admit
I'd looked for something like from butyl alcohol and so on. 
I have understood that these are really nasty ones, so if I find synth that is within my limits, I have a remote place several miles away from any
human existence and proper gear (chem suits and full resp masks) where I would attempt to synthetize it. I'm pretty interested in these nasties and
saw that phenylisonitrile could be made quite more easily from aniline and chloroform. How "bad" would you compare phenyl- and t-butyl isonitriles in
terms of stench?
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