video tutorial Acetylglycine and preparing an oxazolone heterocycle

Name: video tutorial - Acetylglycine and preparing an oxazolone heterocycle
Uploaded: 2025-12-11T09:03:44.116Z
Duration: 14 min 43 s
Description: So this will be a video in two parts....We've covered off how to make this in a few different videos before.

Two-part protocol: (1) prepare acetylglycine by acetylating glycine with acetic anhydride in a small water solvent to give a white precipitate; 72% yield (5.6 g from 5 g glycine) after crystallization and drying.
(2) perform the Erlenmeyer reaction: acetylglycine, vanillin, anhydrous sodium acetate, and acetic anhydride heated to form a yellow crystalline oxazolone product (aniline-substituted methyl oxazole-5-one); 55% yield (6.2 g from acetylglycine).
Workup and purification: hot chloroform extraction, cooling to precipitate product, washes with petroleum ether to remove acetic acid; final drying to yield a bright yellow solid; isolation requires careful control to avoid hydrolysis or oil formation.
Mechanistic notes: acetylglycine cyclizes to an azelaptone (oxazolone), which then condenses with vanillin in the presence of acetic anhydride and sodium acetate, eliminating two waters and forming the target heterocycle; acetic anhydride is converted to acetic acid.
Further chemistry: alkaline hydrolysis of the oxazolone product yields a cinnamic acid derivative and a tyrosine-like amino acid analogue, drawing parallels to dopamine structure; potential for follow-up reactions.