Triethylamine hydrochloride → HCID 21219679, compound

HRID 1584684Notes

Reaction equation

[C:1]([P:3](=[O:10])([O:7]CC)[O:4][CH2:5][CH3:6])#[N:2].Cl.[CH2:12]([N:14]([CH2:17][CH3:18])[CH2:15][CH3:16])[CH3:13]>CC(N(C)C)=O>[CH2:5]([O:4][P:3]([C:1]#[N:2])(=[O:7])[O-:10])[CH3:6].[CH2:12]([NH+:14]([CH2:17][CH3:18])[CH2:15][CH3:16])[CH3:13]

Participants

Conditions

Temperature: 80 °C

Procedure

Diethyl cyanophosphonate (0.50 g, 3.06 mmol) and triethylamine hydrochloride (0.421 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 0.42 g (67% yield) of a viscous residue which was analyzed by NMR and mass spectrometry without additional purification. 31P NMR (D2O) δ (ppm) major peak (94.7%) -19.6 (t, 3JPH =9.3 Hz), minor peak (5.3%) -12.1; 1H NMR (D2O) δ (ppm) 1.25 (tr), 3.20 (q), and 4.05 (qnt); 13C NMR (D2O) δ (ppm) 119.9 (d, 1JCP =174.35 Hz), 63.9 (d, 2JCP =6.6 Hz), 47.0 (t, J=4.0 Hz) 16.0 (d, 3JCP =6.8 Hz), 9.1 (s). Mass spectral analysis (FAB+, thioglycerol) detected a peak at m/z 338.4, corresponding to the complex species [[+HN(C2H5 )3 ]2 --O(OC2H5)POCN]+ !, the presence of a cation at m/z 102 [[HN(C2H5)3 ]+ ] and an anionic species (FAB- thioglycerol) at m/z 133.9 [NCP(O)(OC2H5)O - ], its protonated dimer at m/z 268.9 [(H+) O(OC2H5)POCN- ][O(OC2H5)POCN]-, and to the cluster [[+HN(C2H5)3 ]O(OC2H5)POCN- ][O(OC2H5)POCN]- at m/z 370.1.

Workup

customThen dimethylacetamide was removed under vacuum

Sources & evidence

ORD record: ord-29245af8a4984d3889ee532faba1549e
Source dataset: uspto-grants-1999_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05935542

Reaction notes

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