Allylamine → HCID 7325929, compound

Participants

Reaction Steps

A functional monomer was prepared in the following manner, and was used in Example 15 to introduce activated ester groups on the backbone of the polymer. Glutaric anhydride, 20 g (0.175 mole), was dissolved in 100 ml chloroform. The glutaric anhydride solution was cooled to <10° C. using an ice bath. Allyl amine, 10 g (0.177 mole), was dissolved in 50 ml chloroform and added to the cooled solution of glutaric anhydride with stirring. The addition rate of allyl amine was adjusted to keep the reaction temperature <10° C. After the allyl amine addition was completed, the reaction solution was allowed to come to room temperature while stirring overnight. After removing the solvent, the 5-oxo-6-aza-8-nonenoic acid isolated amounted to 31.4 g (105% crude) with a dual DSC melting point of 35.1° C. and 44.9° C. NMR analysis at 300 MHz was consistent with the desired product: 1H NMR (CDCl3) amide proton 6.19 (b, 1H), vinyl protons 5.13, 5.81 (m, 3H), methylene adjacent to amide N 3.85 (m, 2H), methylenes adjacent to carbonyls 2.29, 2.39 (t; 4H), and central methylene 1.9. (m, 2H).

Provenance & Evidence