V. Lachkova et al. · N-Dimethylphosphinoyl-substituted Aminomethanephosphonic Acids
563
was heated to reflux. 1.20 g (40 mmol) of paraformaldehyde N-Benzyl-N-dimethyphosphinoylmethyl-aminomethane-
was then added in four portions with stirring and the mix- phosphonic acid hydrochloride (3 · HCl)
ture refluxed for 2.5 h. The water and HCl were removed
From 1.18 g (6 mmol) of N-benzylaminomethyl-dimeth-
ylphosphine oxide, 0.49 g (6 mmol) of phosphorous acid,
2 mL of water, 1.5 mL of concentrated hydrochloric acid,
and 0.36 g (12 mmol) of paraformaldehyde according to the
procedure described above a colorless, transparent, viscous
liquid was obtained, which was washed with ethanol. The
residue was recrystallized from an ethanol/isopropananol
mixture. Yield 1.15 g (58 %). M. p. 158 – 159 ◦C.
by distillation under reduced pres◦sure. The colorless crude
solid residue melted at 179 – 187 C. It was purified by re-
crystallization from aqueous ethanol. Yield 2.24 g (76 %).
M. p. 187 – 189 ◦C.
[3-(Dimethylphosphinoyl)propyl]imino-bis(methanephos-
phonic acid) (2)
From 1.49 g (11 mmol) of 3-aminopropyl-dimethyl-
phosphine oxide, 1.80 g (22 mmol) of phosphorous acid,
2 mL of water, 2 mL of concentrated hydrochloric acid,
and 1.31 g (44 mmol) of paraformaldehyde, according to
the previously described procedure, a light-yellow viscous
crude product was obtained. It was stirred with diethyl ether,
and the solid product formed was filtered, washed with
diethyl ether and dried. Yield 3.10 g (83 %). M. p. 234 –
Acknowledgements
This study was supported by the Deutsche Forschungs-
gemeinschaft, Bonn-Bad Godesberg, Germany. The authors
thank Prof. G. Ha¨gele for the help in the interpretation of
NMR spectra, Prof. M. Arnaudov for the help in the dis-
cussions of IR spectra and Ms. Hammes for support dur-
ing the X-ray data collections. Thanks are due to Dr. H.-J.
Kleiner (formerly Hoechst AG, Frankfurt/Main, Germany)
for kindly providing 3-aminopropyl-dimethylphosphine
oxide.
◦
235 C. After recrystallization from ethanol-water the col-
orless crystalline compound had a constant melting point
237 – 238 ◦C.
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