deuterated analogue of 2,6-dichlorobenzamide?

Question

Where can I get deuterated analogue of 2,6-dichlorobenzamide, which is degradation product of herbicide dichlobenil?

On the ring would be only acceptable due to effect of H exchange on NH2. I need the compound for calibration of GC-MS by internal standard method. All commercial suppliers I know don’t have such on-ring deuterated 2,6-dichlorobenzamide. Custom synthesis isn’t option because of high price.

Answer 1

Deuterated where? If for instance you mean on the NH2, you can probably prepare this from the protic version by treatment with something like two equivalents of LDA, then quenching with D2O or similar. Or treating the acid chloride with two equivalents of ND3.

On the ring may be a little harder, it may be possible to buy the acid and then proceed as before if you want full D incorporation.

I see your point Mauricio P, however, *if* the databases have been searched, as per "All commercial suppliers I know don’t have such on-ring deuterated 2,6-dichlorobenzamide. Custom synthesis isn’t option because of high price." then making it yourself might be the way to go. Certainly when I've used Scifinder and equivalents before they've mentioned if the product is commercially available. Not all compounds have been made, much less specifically labelled ones for specific tasks.

The acid seems to be available from http://www.medicalisotopes.com/Product_Details.asp?find=2389

I can't see much ND <-> NH exchange going on, once you have the amide, but if you don't need it there, it's less of a problem

What access do you have to synthetic labs - perhaps a collaboration is up for grabs with someone else?

Answer 2

HE ask where can he get it not how to synthesize it. I have seen deuterated amides and aromatics at the chemistry department of UCLA, I don't have the number with me right now but if you call them you can contact the lab assistant because they can tell you what company provides them the compounds. I hope this works, I have no idea what other company (using Scifinder or Cambridgesoft products to search a database is not going to get you a bottle of that stuff, obvious really).

Answer 3

If it's the NH2 you want deuterated dissolve the proteo stuff in DCM and give it a couple of washes with D2O, remove solvent
If the ring then you'll need to make it-not to hard
disslove proteo stuff in DCM, wash with several portions of D2SO4 to effect deuterium exchange to get d5-benzamide then back wash wih H2O to get back the NH2 or
dissolve 2-bromo-1,4-dichlorobenene in DCM and wash with several portions of D2SO4to effect the deutertum exchange then using bis-(N-methylbenzothiazolium) palladium diiodide, PPh3 ethyldiisopropylamine and dibutylamine in diethylacetamide at reflux under carbon monoxide (which would let you C13 label as well)will give the dibutylbenzamide. Hydrolyse, make acid chloride then reactwith ammonia to get d3 benzamide

or use the acid available above

Answer 4

depends on where you want it deuterated and how good of a chemist you are. try searching on scifinder and call aldrich and see what they say. they give advice for free if you're clever

Answer 5

Tescos

Answer 6

try the chemist

Answer 7

It depends what you want it for, you don't wan't to blow anything up, do you?