Many methods of monoacylation of primary amides were studied ; one, the sulphuric acid-catalysed reaction of amides with anhydrides at 100". w a s found to be very general. Several new acyclic imides were synthesised, including compounds as diverse as N-acetylvaleramide, N-valeryl-4-methylvaleramide, and 3a-acetoxy-N-acetylcholanamide. In two cases symmetrical imides related to the anhydride used were identified as minor by-products of the synthesis of mixed imides.WHEREAS cyclic imides such as succinimide and pht.ha1imide are well known and useful compounds, acyclic imides (A'-acylamides, R1*CO*NH*CO*RA) have been practically ignored. The reason is that while a way to make any desired imide can eventually be found, all attempts to devise a general method have fai1ed.lWe are trying to develop the photorearrangement of N-chloro-imides to 4-~hloro-imides,~ which are useful for conversion into lactones and pyrrolidone~,~ into a low and variable yields. Conversions, at least as measured by g.l.c., were improved by lowering the reaction temperature and changing the catalyst to acetyl bromide, but isolation of pure products on a preparative scale remained difficult and tedious. Results of these experiments are given in Table 1, nos. 7,9,10, 13, 17, and 23.The by-products of these reactions may often include not only nitriles, acids and tar, but also other imides.
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