Carbon Dioxide → HCID 131718373, compound

Participants

Reaction Steps

A Fischer-Porter bottle was charged with 0.65 g (5 mmol) of octyl amine, 1.17 g of P1 -tBu (5 mmol), 0.51 g of triethylamine, 25 mL of acetonitrile and 184 mg (1 mmol) of tridecane as an internal standard. The bottle was pressurized to 80 psig with carbon dioxide and the solution was stirred for 30 minutes at room temperature. A second Fischer-Porter bottle was charged with 4 g (28 mmol) of P2O5 (phosphorus pentoxide), 0.86 mL water, 4 mL of triethylamine and 25 mL of acetonitrile then pressurized to 80 psig with CO2. The P2O5 /water/triethylamine mixture gave a dark brown solution and the carbamate solution was added rapidly to this mixture at room temperature. An aliquot was taken after five minutes and diluted with diethyl ether prior to G.C. analysis which indicated a yield of 15% octyl isocyanate. The reaction mixture was stirred for an additional 18 hours during which time the yield of octyl isocyanate increased to 98.8% by G.C. analysis.

Provenance & Evidence