Tuesday 8 March 2016

Salicylamide

Salicylamide, or 2-hydroxybenzamide, is an uncommon painkiller similar to aspirin.
It's mainly used as a precursor to the antihypertensive drugs Medroxalol and Labetalol.
I'm interested in using salicylamide to make benzoxazolone and salicylonitrile.

Crude salicylamide can be made from salicylic acid and urea. I tried this out:

To a 250ml conical flask, I added 10g of salicylic acid, 13g of urea and 1g of boric acid. I heated the mixture until everything was molten. I kept heating the mixture at around 180 C for 1 hour 40 minutes. Then I added 55ml of 18g/L ammonia solution and boiled the mixture for 5 minutes. I placed the mixture in an ice bath to cool it. After 10 minutes in the ice bath, I took the mixture out and added 40ml of 33% hydrochloric acid. Immediately an off-white precipitate of salicylamide formed. I filtered off the salicylamide and dried it. I got 11g, which would be a yield of 94% if the product was pure.

After a few tests, I found it was contaminated with salicylic acid, but that's ok for my purposes.


here's a link to the reaction mechanism
http://www.sciencemadness.org/talk/files.php?pid=416184&aid=42721

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