The Hive => Chemicals & Equipment => Topic started by: wimpy on May 26, 2004, 09:27:00 PM
Title: Benzamide from Urea and Benzoic Acid
Post by: wimpy 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 ...
Title: aniline: http://www.rhodium.ws/chemistry/nitrob...
Post by: ApprenticeCook on May 27, 2004, 03:18:00 AM
(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...
Title: I recommend
Post by: ning 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.
Title: Hey ApprenticeCook, ning!
Post by: wimpy on May 27, 2004, 08:22:00 PM
Hey ApprenticeCook, ning! Thanks a lot, that might help!
Title: Er, do i get this right?
Post by: wimpy 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!
Title: It would seem to be the case
Post by: yei on August 05, 2004, 06:33:00 PM
just make sure to use equal moles and not simply equal weights
Title: suppose one needs o-bromobenzamide and they...
Post by: bbeeasheets 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?
Title: No
Post by: Nicodem 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.
Title: Probably one would start from toluene
Post by: yei 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.