Based on the strategy of liquid-phase synthesis, polyethylene glycol (PEG) 4000 was used to load [1,3, 5] chlorotriazine by etherification, forming a novel soluble polymer-supported reagent I which reacted with 4-io-dobenzoic acid in the presence ofN- methylmophorpholine to generate the activated ester n. From the ester n, the intermediate Ⅲwas produced by the Sonogashira coupling reaction with terminal alkynes under the co-catalysts of Pd(OAc)2 and Cul. These final products of alkynyl benzamide derivatives IV were obtained by the cleavage of support with primary or second amines. Due to the long and flexible chain of PEG, PEG supported substrates could maintain high reactivity so that the reactions involved could be carried out under mild conditions in good yields. Both aliphatic and aromatic amines were effective, but aromatic amine took longer time to yield the corresponding amide. Both primary and secondary amines were readily aminolysized, but secondary amine gave relatively low yield. It appeared that the aminolysis had good selectivity since the intermediate Ⅲwas more readily attacked by N-nucleophiles than by 0- nucleophiles. Besides, PEG 4000 supported reagentⅠ could be more conveniently operated than [1,3,5]-chlorotriazine without the strong irritation.

Key words: POLYGLYCOL;BENZAMIDE P;TRIAZINE P;CHLORINE COMPOUNDS, PALLADIUM;COPPER