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Dichlorocarbene, which is generated by reaction of CHCl 3 with MeONa, is likely to chlorinate DMF to produce the Vilsmeier-Haack-Arnold salt that, in the presence of excess MeONa, gives DMF dimethylacetal (2). This latter reacts with primary amides to yield the corresponding N,N-dimethyl-N -acylformamidines. Solid state structure of N-[(dimethylamino)methylene]phenoxyacetamide (4) obtained...
In the preparation of 5-[(2-hydroxyacyl)amino]-2,4,6-triiodo-1,3-benzenedicarboxamides 1a-h from 2a-h two conditions using stoichiometric amounts of base (method A - aq NaOH at 50 °C; method B - MeONa in DMF at r. t.) were used. Yields are good to excellent provided that the right conditions are chosen. Primary amides 2a,b give 1a,b with method B only, whereas with method A extensive hydrolysis...
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