Aminoamidines - 7. 2-(Arylaminomethyl)imidazolines and their acylated derivatives

2-(Arylaminomethyl)imidazolines were prepared by the reaction of arylaminoacetonitriles with ethylenediamine in the presence of catalytic amounts of P₂S₅. These imidazolines react with aroyl chlorides (1 : 2 ratio) to give diacylation products. In the case of a 1 : 1 mole ratio as well as on treatment with Ac₂O in Et₃N, monoacylation at the imidazoline ring predominantly occurs. Isomeric 2-(N-benzoyl-N-arylaminomethyl)imidazolines were obtained from N-benzoyl-N-arylaminoacetonitriles by the Pinner method. 2-(N-Aroyl-N-arylaminomethyl)benzimidazoles and -benzoxazoles were synthesized in a similar way.