2-Aminopropanol → 2,2'-(1,3-Phenylene)bis(4-methyl-4,5-dihydro-1,3-oxazole)

Participants

Reaction Conditions

Reaction Steps

50 g of isophthalic acid is refluxed at 165° C. (329° F.) for 18 hr in 150 mL of 2-amino-1-propanol. The bulk of the excess amino alcohol is then distilled off and the remaining viscous liquid dissolved in 200 mL of 2% NaOH. The resulting bis-N-(1-methyl-2-hydroxyethyl)isophthalamide is then precipitated in acetone, filtered and dried. To 10 g of the aforementioned diamide is slowly added 300 mL of thionyl chloride with stirring. The mixture is then heated to reflux (79° C., 174° F.) for approximately 1 hour, after which time the homogenous yellow solution is cooled and poured into diethylether to precipitate the 4,4'-dimethyl-2,2'-(1,3-phenylene)bis(oxazoline) hydrochloride salt. The salt is neutralized using 20% NaOH and the free base extracted into ether. The organic phase is then dried and evaporated to give 4,4'-dimethyl-2,2'-(1,3-phenylene)bis(oxazoline).

Provenance & Evidence