Diethyl Ether → HCID 21219682, compound

HRID 1584686Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

Diethyl cyanophosphonate (0.50 g, 3.06 mmol) and trimethylsulfoxonium iodide (0.673 g, 3.06 mmol) were added to dimethylacetamide (1 mL) which was heated to 80° C. for 1 hour. Then ether (9 mL) containing 1 mL of acetone was added to give 0.47 g (78% yield) of a viscous residue which was crystallized within 15 hours. It was washed by CH2Cl2 and dried under vacuum, and analyzed by NMR and mass spectrometry. 31P NMR (D2O) δ (ppm) -19.7 (t, 3JPH =9.15 Hz); 1H NMR (D2O) δ (ppm) 1.22 (t), 3.78 (s), and 4.05 (qnt); 13C NMR (D2O) δ (ppm) 118.1 (d, 1JCP =178.9 Hz), 63.3 (d, 1JCP =6.3 Hz), 39.5, 15.0 (d, 3JCP =6.87 Hz). Mass spectral analysis (FAB+, DTT:DTE, 1:1) detected a peak at m/z 320.1, corresponding to the complex [[+OS(CH3)3 -O(OC2H5)POCN] [OS(CH3)3 ]+ ], the presence of a cation at m/z 93 ([OS(CH3)3 ]+) and an anionic species (FAB-, DTT:DTE, 1:1) at m/z 134 [NCP(O)(OC2H5)O - ].

Workup

additionwas added

Sources & evidence

ORD record: ord-0b99bcc9b220419391ff3932a31c69e5
Source dataset: uspto-grants-1999_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05935542

Reaction notes

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