Thread: will this type of reaction occur?

Hiyas

Would it be possible for this type of reaction to occur?

F3CCO.OCO.CF3 + 2 H2NOH.HCl + 2 NaOH --------> 2 F3CCO.ONH2 + 2 H2O + 2 NaCl

I cant find any literature on the F3CCO.ONH2 at all, but I need to make it so I can carry out my practical work for my dissertation. Im really stuck on this at the moment and would greatly appreciate any input. Also as I cant find the MSDS for the F3CCO.ONH2, I would have to pick a similar compound, would I be best getting the MSDS for H3CCO.ONH2 or something like that if it exhists? or would I need to keep the F atoms on?
Thanks again

Ok, if I'm understanding this right, you're treating trifluoroacetic anhydride with hydroxylamine in basic conditions...

I don't think you can make it that way, it's the N on hydroxylamine that's more nucleophilic and I reckon you'll get the amide (CF3C(O)NHOH)) but that's just a guess. Why are you trying to make this compound?

Also, the standard procedure for hazard data with unknown compounds is to assume toxic - referencing similar compounds is no use, for example you'll be generating trifluoroacetate in the reaction (probably), trifluoroacetic acid is 100,000 times more acidic than acetic acid!

Hi Matt thanks for the reply,

the NAOH is only added to remove the HCl from the hydroxylamine hydrochloride.

Im trying to make the compound so I can react it with the =O sticking off a testosterone molecule, I know that the N from the NH2 part of the molecule will swap places with the =O on the testosterone, as ive seen a paper on this reaction, only problem I have is I need to get the F's into the molecule too, I can only attack the testosterone at the =O section, no other parts.

Thanks for the help with the safety stuff, Ill just note that it is toxic /harmful.

I need to get the fluorine onto the testosterone so I can see it with SEM

Hmm. Have you looked into the possibility of using something like trifluoroethylamine (CF3CH2NH2) instead? Simple acid catalysed reaction with testosterone gives you what you need I think...



Is that the sort of thing you're after? I have no idea how expensive or safe it is (then again if you were gonna use trifluoroacetic anhydride I doubt it'll be worse than that). Also I'm not sure how useful it'll be either, depends on how strong the effect of the CF3 group is. Just a thought anyway.

thanks matt, this could be really useful, ill run it by my supervisor, thanks

to me it does look alot easier :-D

In theory it should be... I don't have an Aldrich catalogue to hand but I can't imagine it'll be that pricey, even then I'd guess you're not gonna use much of it at once.

Let me know if it's of any use, it'd be nice to know that all that organic crap I've been taught is actually applicable to real life :P

just checking it out on sigma aldrich website at the moment. Just incase you didnt know, you can get MSDS stuff from their website, its a good database they have.

Ive mailed my supervisor, so i should find out monday, ill post here when i know, thanks again.

edit: yeah regarding quantities it will be less than 5grams, probably nearer 1gram, but i was going to make 5grams of the other product, so my supervisor could "play" with it.

Cool. I had a quick look on the Sigma Aldrich website too after I posted that actually... shame they don't have stuff like solubility data to hand either. Would be useful and I could have my question I posted earlier (about Fe(acac)2) answered... even the all-knowing CRC Handbook of Chemistry and Physics doesn't know. It's not cheap and I'll be using it in bulk (>50 g probably) so I don't want to waste my supervisor's budget money if it's going to turn out useless... ah Chemistry :P

Ive spoken to my supervisor, who said it seems like it could work, but he has told me to find out how stable the product is with water, im not too sure how to do this, as there is no literature I can find on the product, any ideas?

Well since you can buy it as the free base or the hydrochloride salt I rather doubt it has any incompatibilities with water.

hmm its difficult to tell but this reaction should proceed as its product is all clear...