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2-Substituted-2,3-dihydro-5-propoxy-1H-1,3,2-benzodiazaphosphole 2-Oxides
279
(1962).
1.66g, 0.01 mole) and triethylamine (2.02 g, 0.02 mole) in dry
toluene (50 ml). After the addition, the temperature of the reac-
tion mixture was allowed to raise slowly to 45-55 °C and stirring
was continued for an additional 3-4 hours. Progress of the reac-
tion was monitored by tlc analysis. The reaction mixture was fil-
tered to separate triethylamine hydrochloride and the solvent was
evaporated from the filtrate under reduced pressure. The residue
after washing with water was recrystallised from methanol to
give 1.75 g of pure 4d in 56% yield, mp 212-214 °C. Physical
and spectral data of 4d are given in Tables 1-4. 4a-i were pre-
pared by this procedure.
[3] R. I. Zhadanov, W. A. Buina, N. A. Kapitanova and I. A.
Nuretdinov, Synthesis, 269 (1979).
[4] H. Arnold, F. Bourseaux and N. Brock, Arzneimittel Forsch,
11, 143 (1961).
[5] O. M. Friedman, Z. B. Papanastassiou and R. S. Levi, J. Med.
Chem., 6, 82 (1963).
[6] H. Zimmer and A. Sill, Prog. Drug. Res, 5, 150 (1964).
[7] P. Hsu, I. S. Kao, J. S. Tsai, C. H.Chou, M. C. Liu, M. L. Sheu,
T. Y. Meug, Y. F. Jen, R. C. Pan and S. W. Li, Sci. Sinica (Peking), 13, 789
(1964).
[8] T. L. Lemke and D. Boring, J. Heterocyclic Chem., 17, 1455
(1980).
2-(2-Chlorophenoxy-2,3-dihydro-1H-1,3,2-benzodiazaphosp-
hole 2-Oxide (6e).
[9] C. C.Beard, E. A. Averkim, C. A. Dvorak, J. A. Edwards, J. H.
Fried, J. G. Kilian, R. A. Schiltz, T. P. Kistner, J. H.Drudge, E. T. Lyons,
M. L. Sharp and R. M. Corwin, J. Med. Chem., 18, 1164 (1975).
[10] R. J. Gyurik and V. J. Theodorides, U.S. Patent, 3 915 986
(1975); Chem. Abstr., 84, 31074r (1976).
[11] Smithkline and French Laboratories, British Patent 1 123 317
(1968); Chem. Abstr., 69, 96722k (1968).
[12] L. C. Thomas and R. A. Chittenden, Chem. Soc. (London),
1913 (1961).
[13] R. A. Nyquist, Spectrochim Acta., 19, 713 (1963).
[14] L. C. Thomas and R. A. Chittenden, Spectrochim Acta., 20,
489 (1964).
[15] L. C. Thomas, The Interpretation of the Infrared spectra of
Organophosphorus Compounds, Heydon, London (1974).
[16] R. M.Silverstein, G. C. Bassler and T. C. Morrill,
Spectrometric Identification of Organic Compounds, John Wiley and
Sons, New York (1981).
A solution of 2-chlorophenyl phosphorodichloridate (5e,
2.46 g, 0.01 mole ) in dry toluene (25 ml) was added dropwise
over 20 minutes to a stirred solution of 3 (1.66 g, 0.01 mole) and
triethylamine (2.02 g, 0.02 mole) in dry toluene (60 ml). After
the addition, the temperature was slowly raised to 55-65 °C and
stirred for 6-7 hours. TLC analysis (silica gel) was used to mon-
itor the progress of the reaction. The product was isolated by the
procedure described above and purified by trituration with
methanol to afford 1.55 g (46%) of 6e, mp 194-196 °C. Physical
and spectral data of 6e are given in Tables 1-4. 6a-g were pre-
pared by this procedure.
Acknowledgements.
[17] R. M. Silverstein and F. X. Webster, Spectrometric
Identification of Organic compounds, 6th edition, Wiley, New York
(1998).
[18] N. Muller, P. C. Lauterbur and J. Goldenson, J. Am. Chem.
Soc., 78, 3557 (1956).
[19] F. Ramirez, V. A. U. Prasad and J. F. Maracek, J. Am.Chem.
Soc, 96, 7269 (1979).
[20] P. A. Odorissio, S. D. Pastor and J. D. Spivack, Phosphorus
and Sulfur, 20, 273 (1984).
The authors express their thanks to Central Drug Research
Institute, Lucknow, India for elemental analyses, Dr.C.V.N.Rao,
Department of Biochemistry, University of Kuwait, Kuwait for
recording EI mass spectra, T. Chandrasekhar, Department of
Botany, S.V.University, Tirupati for microbial studies and
Dr.C.N.Raju, Department of Chemical Engineering,
S.V.University, Tirupati for useful discussions.
[21] D. G.Gorenstein and R. Rowell, J. Am. Chem. Soc, 101, 4925
(1979).
REFERENCES AND NOTES
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Publications, USA, 5th edition, p. 134 (1990).
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