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Chemistry Forums for Students => Organic Chemistry Forum => Organic Chemistry Forum for Graduate Students and Professionals => Topic started by: Introspect on October 01, 2014, 10:27:11 AM

Title: Succinimide
Post by: Introspect on October 01, 2014, 10:27:11 AM

Hello,

let's suppose you urgently (within a day or two) need a couple of grams of relatively pure succinimide. Nobody at your department has it, however you have around 200 grams of both NCS and N-hydroxysuccinimide in your lab.

Is there some easy way to obtain succinimide from one these two or prepare it in some relatively simple and quick way? Buying is not a possible option, since we usually wait around 10 days for ordered merchandise.

Title: Re: Succinimide
Post by: discodermolide on October 01, 2014, 10:40:17 AM

Nothing springs immediately to mind, do you have any particular ideas?

Title: Re: Succinimide
Post by: Introspect on October 01, 2014, 10:52:42 AM

The best I was able to find is this:

http://www.orgsyn.org/demo.aspx?prep=cv2p0562

but the issue in here is that we have no succinic acid, at least not thsi week which makes that procedure useless for now.

I'd really appreciate if someone could share some procedure which uses NCS or N-hydroxysuccinimide.

Title: Re: Succinimide
Post by: discodermolide on October 01, 2014, 12:01:16 PM

Have you got any toluene and carbon tetrachloride?

Title: Re: Succinimide
Post by: Introspect on October 01, 2014, 03:47:11 PM

Yep, a couple of liters of both.

Title: Re: Succinimide
Post by: discodermolide on October 01, 2014, 04:05:23 PM

Then see if you can find any info. of the photochemical bromination of toluene with NBS in CCl₄.

Title: Re: Succinimide
Post by: Dan on October 02, 2014, 03:01:16 AM

Reduction of NCS should be very easy. You can just look for any chlorination reaction that uses NCS, because the stoichiometric byproduct is succinimide.

I've not looked it up, but I'd imagine there are lots of inorganic reductants that would work as well, like Zn, Fe, Sn(II), H₂ + Pd, thiosulfates, bisulfites etc. - the N-Cl bond is not very strong.

Title: Re: Succinimide
Post by: Introspect on October 03, 2014, 11:04:44 AM

Thank you all for the suggestions.

I found that we have some succinic acid, so I'll be doing the procedure described in the link I pasted above.

I have one question, what does the term "downward" distillation mentioned in that procedure mean?