Alchemist
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Salicylamide
Hello all,
Has anyone actually made Salicylamide?
I was thinking of using salicylic acid with Urea, but DO NOT know exactly how to go about it. Are they melted together, refluxed with some solvent, or
what ? Any help would really be appreacted!
Thanks, The Alchemist.....
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Nicodem
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There was a thread discussing the topic of amide preparations with urea:
https://sciencemadness.org/talk/viewthread.php?tid=4201
With salicylic acid you might end up with a complex mixture or you might even obtain 1,3-benzoxazine-2,4-dione as the major product instead of
salicylamide. You might consider preparing salicylamide from methyl salycilate as an alternative (see Inorganic Chemistry, 42 (2003)
4401-4408).
Off topic, but there is also an interesting reaction (to me at least) where urea can be used for direct electrophilic ortho carboxamidation of phenol:
Patent CN1923800
| Quote: | | CA abstract: The title method includes adding solid alkali catalyst into a mixt. of phenol and urea at a phenol/urea molar ratio of (1-100):1 and a
catalyst/urea molar ratio of (0.001-10):1, and reacting at 140-220C and 0.1-3.5 MPa for 1-24 h to obtain the final product. Thus, reaction of phenol
with urea in the presence of CaO at 200 and 1.6MPa for 3 h gave 85.73% salicylamide. |
The catalyst is prepared according to CN101053830:
| Quote: | | CA abstract: The title catalyst is composed of (by wt.%) CaO 10.0-30.0 and ZnO 70.0-90.0. The title method comprises (1) prepg. a 0.1-0.3 M Ca(NO3)2
soln., a 0.1-0.3 M Zn(NO3)2 soln. and a 10-25 vol.% ammonia soln., resp., (2) simultaneously dropping the Ca(NO3)2 soln., Zn(NO3)2 soln. and ammonia
soln. in a reactor, pptg. at pH 8.5-13 and 30-80, aging for 1-5 h, washing with water to neutrality, and filtering, and (3) drying at 90-110, and
calcining at 350-800 for 2-5 h. Salicylamide is synthesized by reacting urea with phenol at a molar ratio of 1 : (1-50) in the presence of 0.5-30
wt.% the catalyst at 100-250 for 2-24 h, dilg. and centrifuging. The method has the advantages of available raw materials, simple operation, high
selectivity, mild reaction conditions, etc. |
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