Phosphonicacid,(carbamoylmethyl)-,diethylester

2-Chloroacetamide (5.01 g, 53.6 mmol) and triethyl phosphite (9.19 mL, 53.6 mmol) were heated at reflux in o-xylene (14 mL) for 3.5 h. The solvent was removed under reduced pressure to afford a dark brown tar-like residue. The residue was taken up in dichloromethane and filtered through a short column of silica. The filtrate was concentrated and the solid recrystallised from ethyl acetate/pentane to afford diethyl carbamoylmethylphosphonate (3.42 g, 33percent) as light brown crystals. ‘H NMR (200 MHz, DMSO-d6) ö 7.35 (br s, 1H); 7.02 (br s, 1H); 4.02 (dq, 4H, J=7.1 Hz, JpH=1.1 Hz); 2.80(d, 2H, JPH =21.4 Hz); 1.23 (t, 6H, J=7.0 Hz). ‘3C NMR (50 MHz, DMSO-d6) ö 166.0(d, 2Jcp5.1 Hz); 61.5 (d, 2J=6.0 Hz); 34.5 (d, ‘Jp131.6 Hz); 16.2 (d, 3J=6.0 Hz).3’P NMR (81 MHz, DMSO-d6) 23.8. ESIMS: m/z 218 [M+Na]. HRMS calcd forC6H, 4N04P 195.0655, found 195.0653.

Molecular Weight:195.15
XLogP3:-0.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:6
Exact Mass:195.06604493
Monoisotopic Mass:195.06604493
Topological Polar Surface Area:78.6
Heavy Atom Count:12
Complexity:184
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes