Methyl acetanilid iodid

By the further substitution of a group (CHa) in acetanilid, methyl-acetanilid, or exalgine, Cmethyl iodid upon sodium acetanilid, CsHaiNNa CjHsO. It is a crystailine solid, sparingly soluble in. HsO, readily in dilute alcohol. Its odor is faintly aromatic. 

N-Methylacetanilide is obtained in 96% yield by the action of methyl iodide or dimethyl sulfate on the sodium salt of acetanilide. The last compound is prepared from acetanilide and sodium wire in hot benzene. The reaction has been extended to other aliphatic and aromatic N-sub-stituted amides. Sodium hydride serves to convert the amide to its salt, and a variety of simple halides have been successfully employed as alkylating agents, ... 

The ethereal solutions of these iodides do not fume in air, and removal of the solvent gives a liquid, which on further heating evolves dense white fumes, probably of beryllium oxide. Heating changes the alkyl beryllium halides to beryllium dialkyls. All the alkyl halide compounds are decomposed by water, with formation of the corresponding hydrocarbon. When carbon dioxide is passed through ethereal beryllium methyl iodide for three hours, the solution still gives a positive test and no acetic acid is found after hydrolysis. Acetanilide is formed from beryllium methyl iodide and phenyl isocyanate. 

Aniline, acetanilide, benzyl alcohol or methyl benzoate containing a halogen atom in the or /zo-position react with 1 -alkynes in the presence of bis(triphenylphosphine)palladium(II) chloride and copper(I) iodide to give the corresponding o-alkynylbenzenes (e.g. equation 6). Some of the products can be cyclized the aniline derivative 53, for instance, is converted into 2-phenylindole in 99% yield on treatment with a catalytic amount of copper(I) iodide. ... 

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