15572-56-2 → HCID 21219670, compound

HRID 1584683Notes

Reaction equation

HRID 1584683 reaction equation
[C:1]([P:3](=[O:10])([O:7]CC)[O:4][CH2:5][CH3:6])#[N:2].[Cl-].[CH:12]([NH3+:15])([CH3:14])[CH3:13]>CN(C=O)C>[CH2:5]([O:4][P:3]([C:1]#[N:2])(=[O:7])[O-:10])[CH3:6].[CH:12]([NH3+:15])([CH3:14])[CH3:13]

Participants

4

Reactant 2

HCID 2739915572-56-2HCID 76257Diethyl cyanophosphonate

Product 1

HCID 21219670HCID 21219670, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Diethyl cyanophosphonate (0.50 g, 3.06 mmol) and isopropylammonium chloride (0.29 g, 3.03 mmol) were added to DMF (3 mL) and the reaction mixture was stirred overnight. The solvent was removed under reduced pressure to give 0.48 g (88% yield) of an oil which was analyzed by NMR and mass spectrometry without additional purification. 31P NMR (CD2Cl2) δ (ppm) -21.2 (t, 3JPH =8.4 Hz); 13C NMR (CD2Cl2) δ (ppm) 121.0 (d, 1JCP =177.8 Hz), 63.2 (d, 2JCP 6.3 Hz), 42.1 (s), 20.9 (s), 16.0 (d, 3JCP =7.5 Hz). Mass spectral analysis (FAB+TGL) detected the peak at m/z 195, corresponding to the protonated form of the salt [+NH3CH(CH3)2 --O(OC2H5)POCN+H+ ], the presence of the cation at m/z 60 ([NH3CH(CH3)2 ]+) and an anionic species (FAB-, TGL) at m/z 134 [NCP(O)(OC2H5)O- ].

Workup

  1. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-30370708927e420fa16e0c7c8f1c7657
Source dataset
uspto-grants-1999_08
Patent number
US05935542

Reaction notes

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