Dimethylacetamide → HCID 21219668, compound

Participants

Reaction Conditions

Reaction Steps

Diethyl cyanophosphonate (0.50 g, 3.06 mmol) and tetramethylammonium chloride (0.338 g, 3.06 mmol) were added to dimethylacetamide (0.5 mL) which was heated to 80° C. for 3 hours. Then dimethylacetamide was removed under vacuum to give 0.45 g (70% yield) of a viscous residue which was analyzed by NMR and mass spectrometry without additional purification. 31P NMR (CD3CN) δ (ppm) major peak (87%) -22.4 (t, 3JPH =8.8 Hz), minor peaks: -13.0 to -14.0 (10%), -3.0 (3%); 1H NMR (D2O) δ (ppm) 1.30 (t), 3.20 (s), and 4.05 (qnt); 13C NMR (D2O) δ (ppm) 119.7 (d, 1JCP =175.5 Hz), 63.9 (d, 2JCP =6.3 Hz), 55.8 (t, J=4.0 Hz) 16.0 (d, 3J CP =6.87 Hz). Mass spectral analysis (FAB+, thioglycerol) detected a peak at m/z 282.3, corresponding to the complex species [[+N(CH3)4 ]2-O(OC2H5)POCN]+ !, the presence of a cation at m/z 74.1 [[N(CH3)4 ]+ ] and an anionic species (FAB- thioglycerol) at m/z 133.9 [NCP(O)(OC2H5)O- ], and to the cluster [[+N(CH3)4 ] O(OC2H5)POCN- [O(OC2H5)POCN]- at m/z 342.

Provenance & Evidence