Carbon Dioxide → Octyl isocyanate

Participants

Reaction Conditions

Reaction Steps

Carbon dioxide was added subsurface to a dichloromethane (30 mL) solution containing octylamine (n-OctylNH2) (0.04 mol, 5.2 g), N-cyclohexyl-N',N',N",N"-tetraethylguanidine (0.04 mol, 10.2 g) and triethylamine (0.08 mol, 8.0 g) at -10° C. (ice and salt bath) for 1 h at a pressure of 0 psig. The reaction mixture was transferred via cannula all at once under carbon dioxide to the precooled solution of phosphorus oxychloride (0.04 mol, 6.2 g) in 30 mL dichloromethane. After stirring for ca. 30 min at -10° C. the reaction mixture turned yellow-brown and a ppt. formed. The crude reaction was filtered and the filtrate concentrated in vacuo. The residue was extracted with 2×100 mL diethyl ether. The ether layers (light yellow) were concentrated and the residue was distilled under vacuum (ca. 0.1-0.3 torr) collecting product, octyl isocyanate, at 42°-44° C. (3.9 g, 63%) of 99% purity as by GC. IR (neat) 2274 cm-1. 1H NMR (in CDCl3) δ 3.23-3.29 (t, 2H), 1.54-1.63 (m, 2H), 1.23-1.40 (br, 10H), 0.84-0.90 (t, 3H) ppm.

Provenance & Evidence