Methanol → N-2-(2-dimethylaminomethyl-5-methyl-4-thiazolylmethylthio)ethyl-N'-methyl-2-nitro-1,1-ethenediamine

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Reaction Steps

Following the procedure of Example 5, a stirred solution of 1.38 g. of 2-([2-(dimethylaminomethyl)-5-methyl-4-thiazolyl]methylthio)ethylamine in 10 ml. of methanol was treated with N-methyl-1-methylthio-2-nitroethyleneamine. The reaction mixture was kept at room temperature overnight by which time all solids had dissolved. Thin layer chromatography over silica using a 10:10:1 ethyl acetate-methanol-ammonium hydroxide solvent system indicated substantially a single product. The reaction mixture was concentrated by evaporation of the methanol and the resulting gummy yellow residue was triturated with several portions of cold ether, thus providing an off-white gum. Repeated tritration with cold 1,2-dimethoxyethane yielded N-2-([2-(dimethylaminomethyl)-5-methyl-4-thiazolyl]methylthio)ethyl-N'-methyl-2-nitro-1,1-ethenediamine formed in the above reaction melting at about 104°-106° C.

Provenance & Evidence