REACTION OF METHYLHYDRAZINE WITH DIMETHYL CHLOROTHIO-PHOSPHATE

The reaction of 2 equivalents of methylhydrazine with 1 equivalent of (MeO)2P(S)Cl at 0-degrees-C produced the phosphorus hydrazide (MeO)2P( S)NMeNH2 1 in good yield. However, at 25-degrees-C a mixture of three products was obtained according to H-1 and P-31 NMR spectra. The pure individual components were separated by column chromatography. Proton and P-31 NMR analysis revealed them to be 1, (MeO)2P(S)(NMeNH)(S)P(OMe )2 2 and (MeO)2P(S)NHNHMe 3. During the chromatographic separation of 1-3 another component was also eluted in 5-8% yield, H-1, P-31 NMR and FAB mass spectrometric analysis of which indicated it to be (MeO)2P(S )(NMeNH)(O)P(OMe)Me4. New synthetic strategies to produce 2 in good yi elds are also described.