N-phenylbenzimidoyl chlorides

The synthesis of 1,3-selenazoles from A -phenylimidoyl isoselenocyanates has been reported. N-phenylimidoyl isoselenocyanates 94 are prepared from N-phenylbenzamides 92. Treatment of 92 with thionyl chloride affords N-phenylbenzimidoyl chlorides 93, which yield imidoyl isoselenocyanates 94 on reaction with potassium isoselenocyanate. The imidoyl isoselenocyanates 94 were transformed into selenoureas 95 with either ammonia or primary or secondary amines. Reaction of 95 with an activated bromomethylene compound such as bromoacetophenone in the prescence of a base gave the 1,3-selenazole 97 via the salt 96 <00HCA1576>. 

A 4-amino analogue is produced by the action of N-phenylbenzimidoyl chloride on hydroxyacetonitrile in the presence of sodium hydride (equation 149). 

In further reactions of N-phenylbenzimidoyl chloride (56), methyl isothiocyanate and stannic chloride, in nitrobenzene at 110°C, gave 2-phenyl-4-methylthioquinazoline in moderate yield JV-phenyltrichloroacetimidoyl chloride reacted similarly.41 Then, in one of the few reactions that produce a halogenated pyrimidine ring, the chloride (56) with cyanogen bromide and stannic chloride (in nitrobenzene at 150°C) gave 4-bromo-2-phenylquinazo-line in excellent yield.41... 

N-Phenylbenzimidoyl chloride treated with NaHSe in ethanol-dioxane seleno-benzanilide. Y 89%. M. P. Cava and L. E. Saris, Chem. Commun. 1975, 617. 

A soln. of 5-phenyltetrazole and N-phenylbenzimidoyl chloride in anhydrous pyridine healed slowly and reflnxed several min. until Nj-evolution ceases 3,4,5-triphenyl-l,2,4-triazole. Y 81%. F. e. s. R. Huisgen, J. Sauer, and M. Seidel, B.95, 2885 (1960). 

N-Phenylbenzimidoyl chloride and SbCls mixed in methylene chloride N-phenylbenzonitrilium hexachloroantimonate. Y 95%. F. e. s. J. E. Gordon and... 

NHC has also been used successfully for the construction of quinoxaline framework in one pot (Scheme 60). The synthesis of 2,3-diarylquinoxalines by the aroylation of N-phenylbenzimidoyl chlorides wi aromahc aldehydes and diamines catalyzed by 3mol% of 1,3-dimethylimidazolium iodide (NHC precursor) has been described by Suzuki et al. [85]. The substrates of the catalytic reaction, i.e., N-phenylbenzimidoyl chlorides, are easily obtained... 

A soln. of equimolar amounts of chloracetic acid and triethylamine in ether added to an ethereal soln. of N-phenylbenzimidoyl chloride, and warmed 2 hrs. at 60° chloracetylbenzoylaniline. Y 95%.— This is a simple procedure for the prepn. of diacylamines. F. e. s. F. Cramer and K. Baer, B. 93, 1231 (1960). 

Mesoionic imidazoles (15) are accessible from the reaction of N-methyl-N-(N -phenylbenzimidoyl)aminoacetonitrile (14) with an acid chloride, followed by sodium bicarbonate treatment. Dry hydrogen chloride converts 14 into the imidazolium salt 16 which can also be transformed into 15, or which, with dilute potassium hydroxide, undergoes a Dimroth rearrangement to a 4-anilinoimidazole (Scheme 4). 

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