Reaction of methylhydrazine with dimethyl chlorothiophosphate
Abstract
The reaction of 2 equivalents of methylhydrazine with 1 equivalent of (MeO)2P(S)Cl at 0 °C produced the phosphorus hydrazide (MeO)2P(S)NMeNH21 in good yield. However, at 25 °C a mixture of three products was obtained according to 1H and 31P NMR spectra. The pure individual components were separated by column chromatography. Proton and 31P NMR analysis revealed them to be 1, (MeO)2P(S)(NMeNH)(S)P(OMe)22 and (MeO)2P(S)NHNHMe 3. During the chromatographic separation of 1–3 another component was also eluted in 5–8% yield, 1H, 31P 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 yields are also described.