Nitrogen → HCID 10014629, compound

Participants

Reaction Steps

To a stirred solution of 150 g (795 mmole) of 4-nitrobenzylamine hydrochloride and 243 ml (176 g, 1.75 mole) of triethylamine in 780 ml of methanol was added gradually (under N2) a solution of 54 ml (68.9 g, 906 mmole) of carbon disulfide in 300 ml of methanol. The internal temperature was maintained below 30° C. during the addition, which took 75 minutes. After an additional hour at room temperature, the reaction mixture was cooled to -10° C. in an ice-MeOH bath as a solution of 50 ml (113 g, 795 mmole) of methyl iodide in 125 ml of methanol was gradually added over about 20 minutes. The cooling bath was removed, and the mixture was allowed to stir at room temperature for 2 hours. It was then concentrated in vacuo to a volume of approximately 500 ml and partioned between 2 L of ether and 2 L of 0.2 N HCl. The ethereal phase was washed with 2 L of saturated aqueous NAGl, dried over. MgSO4, filtered and concentrated to give a yellow solid. Trituration with petroleum ether and drying afforded 187 g (97%) of methyl N-(4-nitrobenzyl)dithiocarbamate, mp 106°-107° C., satisfactory purity by TLC in 2:1 hexane EtOAc; mass spectrum (FAB) m/e 243 (M+1)+.

Provenance & Evidence