wimpy (Stranger)
05-26-04 21:27
No 509774
      Benzamide from Urea and Benzoic Acid     

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 ...

- Stone me if necessary -
 
 
 
 
    ApprenticeCook
(Hive Bee)
05-27-04 03:18
No 509831
      aniline: ../rhodium/nitrob...     

aniline:
../rhodium /nitrobenzene.aniline.html

benzamide:
Post 319342 (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...

Its just my opinion, but no-one listens to me anyway, and rightly so...
 
 
 
 
    ning
(acetaminophanatic)
05-27-04 07:24
No 509870
      I recommend     

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.

We'll all meet someday...on the other side
 
 
 
 
    wimpy
(Stranger)
05-27-04 20:22
No 509955
      Hey ApprenticeCook, ning!     

Hey ApprenticeCook, ning! Thanks a lot, that might help!

- Beware of the Morphail Effect! -
 
 
 
 
    wimpy
(Stranger)
06-08-04 20:43
No 512227
      Er, do i get this right?     

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!

- A: Hey! You are no Chemist! B: Damned! Who betrayed me?-
 
 
 
 
    yei
(Stranger)
08-05-04 18:33
No 523827
      It would seem to be the case     

just make sure to use equal moles and not simply equal weights

It's good to bee back! Don't trust your computer!!
 
 
 
 
    bbeeasheets
(Newbee)
08-10-04 20:57
No 524657
      suppose one needs o-bromobenzamide and they...     

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
(Hive Bee)
08-11-04 15:13
No 524832
      No     

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.

“The real drug-problem is that we need more and better drugs.” – J. Ott
 
 
 
 
    yei
(Stranger)
08-11-04 17:03
No 524848
      Probably one would start from toluene     

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.

It's good to bee back! Don't trust your computer!!