Carbamate → Octyl isocyanate

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), 1 02 g (10 mmol) of triethylamine, 25 mL of acetonitrile and 154 mg (1 mmol) of biphenyl as an internal standard. The bottle was pressurized to 80 psig with carbon dioxide and the solution was stirred for 30 min. at room temperature. A second Fischer-Porter bottle was charged with 0.71 g (5 mmol) of phosphorus pentoxide, and 25 mL of acetonitrile then pressurized to 80 psig with CO2. The carbamate solution was added rapidly to the P2O5 suspension at room temperature causing the P2O5 to dissolve. An aliquot taken after three minutes gave a 22% yield of octyl isocyanate by G.C. analysis. The reaction was monitored for a total of 18 hrs during which time the yield of octyl isocyanate increased to a maximum of 27% (1 hr) and then steadily decreased with formation of the symmetric urea.

Provenance & Evidence