I have a project to synthesis quinazolinone from benzoxazin-4-one and aniline (1 : 3) with mixed solvent DMSO and acetate glacial acid using microwave. To know if this reaction was complete i test it with TLC using eluent Ethyl Acetate and n-Hexane (5 : 2). and when i test it, from the beginning, aniline doesnt appear when im sampling it. why this happened?
Acetic acid reacts with aniline, and prevents it from being detected by some methods but not by other methods.
There are quite a few aspects associated with this question. Decker has already pointed out one. As Decker mentioned, aniline is expected to be in its salt form in glacial acetic acid.
Please think about the adsorbent to use in case of TLC, namely silica / alumina and their variations ( acidic / basic / neutral ).
You may also check, which component is to be used for the monitoring of the reaction. Aniline or the other one ?
Factors that mentioned by Decker and Ashis need to be considered, also you can try tlcs in different polarity of the solvent system e,g., you can check tlc in 20% ethyl acetate with Hexane as solvent system to see aniline in tlc or you can perform tlc after basification a portion of reaction mass .
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