1,1-Bis(methylthio)-2-nitroethylene → 1-(6-Chloro-3-pyridylmethyl)amino-1-methylthio-2-nitroethylene

Participants

Reaction Steps

To a refluxing mixture of 6.61 g of 1,1-bis(methylthio)-2-nitroethylene and 100 ml of acetonitrile was added a solution of 4.28 g of 5-aminomethyl-2-chloropyridine in 10 ml of acetonitrile dropwise over a period of 3 hours and 30 minutes and the whole mixture was further refluxed for 2 hours. After cooling, the insolubles (by-product; 1,1-bis(6-chloro-3-pyridylmethylamino)-2-nitroethylene) were filtered off and the filtrate was concentrated and washed with ethyl acetate to give 4.83 g of 1-(6-chloro-3-pyridylmethylamino)-1-methylthio-2-nitroethylene. The ethyl acetate washings were concentrated and the residue was purified by column chromatography (eluent: dichloromethane-methanol (30:1)) to give a further crop (1.15 g) of the same compound.

Provenance & Evidence