Triethylamine → HCID 131718104, compound

Participants

Reaction Steps

Into a 125 ml reaction flask equipped with a magnetic stirrer, thermometer, condenser and nitrogen atmosphere were placed 5.0 g (0.013 mol) of acid chloride of Example 2 and 50 ml of 2% dimethylformamide in methylene chloride. This mixture was stirred during the addition of 2.9 g (about 0.013 hydroxy equivalents) of RJ® 101 (a styrene/allyl alcohol copolymer from Monsanto having 7.7±0.3 wt % hydroxy content). 2.8 g (0.028 mol) triethylamine were added. The reaction was refluxed for 1.5 hours. The mixture was transferred to a separatory funnel with 150 ml methylene chloride and 100 ml of 5% sodium hydroxide. The phases were separated and the organic phase was further extracted with three 50 ml portions of 5% sodium hydroxide and 50 ml water. The organic solution was dried with anhydrous magnesium sulfate and the solvent stripped using aspirator and high vacuum systems. The product was 4.3 g of light yellow crystals. The solid was redissolved in a minimum amount of methylene chloride and precipitated by dropwise addition to 800 ml of hexane. The solid was isolated by filtration yielding 3.9 g. The infrared spectrum (KBr pellet) showed the carbonyl absorption at 1715 cm-1 (imide and ester). The Tg was determined to be 87.6° C. Molecular weight data obtained from gel permeation chromatography indicated an Mn of 1400 and an Mw of 2100 (based on polystyrene standard). The NMR spectrum demonstrated the presence of the HALS moiety in the high molecular weight material (two singlets at 1.2 and 1.3 ppm) and the presence of aromatic hydrogens from the pendant phenyl groups.

Provenance & Evidence