Triethylamine → HCID 19884929, compound

Participants

Reaction Conditions

Reaction Steps

To a 1 l. one-neck round bottom flask fitted with a nitrogen inlet tube and addition funnel was added 7.05 g (220 mmol) of 1-carboxy-1-phenyl-3-(4-methyl-1-naphthalenyloxy)propane and 400 ml of acetone. To the mixture was added 3.2 ml (22.9 mmol) of triethylamine and the resulting mixture was cooled to approximately 0° C. To the mixture was added 2.2 ml of ethyl chloroformate dropwise. The mixture was stirred 30 minutes at about 0° C. and 2.72 g (41.8 mmol) of sodium azide dissolved and a small amount of water was added dropwise. The mixture was stirred for about 60 minutes at about 0° C. and 200 ml of toluene was added. Water was added to the reaction mixture and the aqueous phase was separated and extracted twice with 200 ml of toluene. The organic extracts were combined, washed with water and a saturated sodium chloride solution, and dried over anhydrous sodium sulfate. The sodium sulfate was removed by filtration, and the filtrate was heated on a steam bath for two hours to induce formation of the isocyanate. The mixture was concentrated under vacuum to provide 7.6 g of the title compound which was used directly in the following reaction.

Provenance & Evidence