Author Topic: Benzamide from Urea and Benzoic Acid  (Read 2093 times)

0 Members and 1 Guest are viewing this topic.

wimpy

  • Guest
Benzamide from Urea and Benzoic Acid
« on: May 26, 2004, 09:27:00 PM »
I'm sorry, can anyone give a more detailed description of the in the "synth for aniline" thread and elsewhere mentioned method for synthesizing Benzamide from Benzoic Acid and Urea? I mean like what procedure, what amounts, and so on? If it's already around here somewhere, i couldn't find it ...


ApprenticeCook

  • Guest
aniline: http://www.rhodium.ws/chemistry/nitrob...
« Reply #1 on: May 27, 2004, 03:18:00 AM »
aniline:

https://www.thevespiary.org/rhodium/Rhodium/chemistry/nitrobenzene.aniline.html



benzamide:

Post 319342 (missing)

(PrimoPyro: "All of those = Yuck", Chemicals & Equipment)


Thats all i found utfse but try google or some such... the hive is not the only place that can help with chemistry you know...


ning

  • Guest
I recommend
« Reply #2 on: May 27, 2004, 07:24:00 AM »
Eleusis's methylamine FAQ.
What you are doing is the same reaction, just on a different substrate.

Methylamine is made by acetic acid + urea --> acetamide, acetamide + NaOCl --> methylamine
Similarly, aniline is made by benzoic acid + urea --> benzamide, benzamide + NaOCl --> aniline.

Will search for papers. Actually, I have some, but will search for more. I believe Org Syn has a few synths of aniline derivatives based on this method.


wimpy

  • Guest
Hey ApprenticeCook, ning!
« Reply #3 on: May 27, 2004, 08:22:00 PM »
Hey ApprenticeCook, ning! Thanks a lot, that might help!


wimpy

  • Guest
Er, do i get this right?
« Reply #4 on: June 08, 2004, 08:43:00 PM »
Er, do i get this right? One could simply replace the Acetic Acid in the "Acetamide from Acetic Acid and Urea" Part of the Methylamine FAQ ("lace 125g Urea and 125g of Acetic Acid in a 500mL round bottom flask ...") and end with Benzamide instead of Acetamide? Hm, or if not, can anybody suggest how to calculate the right method and amounts?
Anyway, thanks a lot, was a very helpful advice in each case!
Any advice wellcome!


yei

  • Guest
It would seem to be the case
« Reply #5 on: August 05, 2004, 06:33:00 PM »
just make sure to use equal moles and not simply equal weights


bbeeasheets

  • Guest
suppose one needs o-bromobenzamide and they...
« Reply #6 on: August 10, 2004, 08:57:00 PM »
suppose one needs o-bromobenzamide and they have synthed benzamide from benzoic acid and urea. is there a good synth from benzamide as a starting reagent?

Nicodem

  • Guest
No
« Reply #7 on: August 11, 2004, 03:13:00 PM »
No, there is no good synthesis of o-bromo-benzamide from benzamide.
There is a nice page on Rhodium's site explaining the direction of electrophylic substitutions on benzene derivatives - UTFSE.


yei

  • Guest
Probably one would start from toluene
« Reply #8 on: August 11, 2004, 05:03:00 PM »
Brominate toluene, then separate the isomers (bleh), oxidize with permanganate to o-bromobenzoic acid, then heat with urea to give benzamide.

If benzonitrile is what you're after (as I would suspect), IIRC heating even more will eventually cause it to throw off water and become o-bromobenzonitrile.

but one needn't make ketamine with that o-halo thing anyway...

if one started with phthalic anhydride, it could bee formed into phthalimide, then hoffmann rearranged to anthranilic acid. Then you could diazotize this to o-anything benzoic acid. No isomer separation, but sounds tiresome to me.

However, anyone interested in ketamine analog research could take real advantage of this technique.