Carbon Dioxide → Octyl isocyanate

Temperature

-10 °C

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.

1. customformed
2. customThe crude reaction
3. filtrationwas filtered
4. concentrationthe filtrate concentrated in vacuo
5. extractionThe residue was extracted with 2×100 mL diethyl ether
6. concentrationThe ether layers (light yellow) were concentrated
7. distillationthe residue was distilled under vacuum (ca. 0.1-0.3 torr)
8. customcollecting product, octyl isocyanate
9. customat 42°-44° C.

ORD record

ord-0d7fbc0d9e7d43b080a4088d0984f13d

Source dataset

uspto-grants-1993_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05189205