Dimethylacetamide → HCID 21219668, compound

HRID 1584685Notes

Reaction equation

[C:1]([P:3](=[O:10])([O:7]CC)[O:4][CH2:5][CH3:6])#[N:2].C[C:12]([N:14]([CH3:16])[CH3:15])=O>[Cl-].C[N+](C)(C)C>[CH2:5]([O:4][P:3]([C:1]#[N:2])(=[O:7])[O-:10])[CH3:6].[CH3:12][N+:14]([CH3:16])([CH3:1])[CH3:15]

Participants

Conditions

Temperature: 80 °C

Procedure

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.

Workup

customThen dimethylacetamide was removed under vacuum

Sources & evidence

ORD record: ord-38423b93d72d469f85459b6777051c21
Source dataset: uspto-grants-1999_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05935542

Reaction notes

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