1714
CHUMACHENKO et al.
3
5-Amino-4-[(morpholine-4-yl)carbonyl]-1-(phenyl-
spectrum, δ, ppm: 4.33 d (4Н, 2СН2, JНН 2.4 Hz),
3
amino)-2,3-dihydro-1H-imidazol-2-one (Vc). Yield
21%, mp 229–231°С. IR spectrum, ν, cm–1: 1644
7.21–7.33 m (10Н, 2С6H5), 9.31 t (2Н, 2NН, JНН
6.2 Hz). 13С NMR spectrum, δС, ppm: 42.91, 127.39,
127.85, 128.77, 139.21, 160.62. Found, %: С 71.48; Н
6.10; N 10.25. С16Н16N2О2. Calculated, %: С 71.62; Н
6.01; N 10.44. M 268.
1
(С=О), 1707 (С=О), 3056–3444 (NH, NH2). Н NMR
spectrum, δ, ppm: 3.40–3.45 m (4Н, 2СН2, morpho-
line), 3.60–3.67 m (4Н, 2СН2, morpholine), 5.98 s
(2Н, NН2), 6.57–6.63 m (2Н, С6H5), 6.80–6.87 m (1Н,
С6H5), 7.17–7.24 m (2Н, С6H5), 8.64 s (1Н, NН), 9.80
s (1Н, NН). 13С NMR spectrum, δС, ppm: 45.36,
66.71, 88.55, 113.02, 120.45, 129.42, 141.80, 147.74,
149.77, 163.23. Found, %: С 55.56; Н 5.39; N 23.01.
С14Н17N5О3. Calculated, %: С 55.44; Н 5.65; N 23.09.
M 303.
N,N'-Bis(2-phenylethyl)ethanediamide (B). Yield
4%, mp 181–183°С (184–185°С [17], 186–188°С
[18]). IR spectrum, ν, cm–1: 1654 (С=О), 3307 (NH).
1Н NMR spectrum, δ, ppm: 2.79 t (4Н, 2СН2, JНН
3
7.5 Hz), 3.35–3.40 m (4Н, 2СН2), 7.18–7.33 m (10Н,
2С6H5), 8.75 t (2Н, 2NН, JНН 5.8 Hz). 13С NMR
3
spectrum, δС, ppm: 35.08, 40.06, 126.63, 128.81,
129.05, 139.58, 160.33. Found, %: С 72.78; Н 6.97; N
9.55. С18Н20N2О2. Calculated, %: С 72.95; Н 6.80; N
9.45. M 296.
3-Alkyl-5-[(morpholine-4-yl)carbonyl]imidazol-
idine-2,4-diones (VIa, VIb). A solution of 2 mmol of
compound Vа or Vb in 10 ml of acetic acid was re-
fluxed for 2 h upon stirring. After cooling, the solvent
was removed under vacuum. The precipitate was
washed with a small amount of water and recrystal-
lized from ethanol.
REFERENCES
1. Koever, J., Timar, T., and Tompa, J., Synthesis, 1994,
no. 11, p. 1124.
3-Benzyl-5-[(morpholine-4-yl)carbonyl]imidazol-
idine-2,4-dione (VIа). Yield 82%, mp 151–153°С. IR
spectrum, ν, cm–1: 1649 (С=О), 1719 (С=О), 1786
(С=О), 3074–3294 (NH). Found, %: С 59.56; Н 5.78;
N 14.01. С15Н17N3О4. Calculated, %: С 59.40; Н 5.65;
N 13.85. M 303.
2. Koever, J., Szilagyi, L., Antus, S., Tompa, J., and
Gunda, T., Heterocycl. Commun., 2002, vol. 8, no. 3,
p. 237.
3. Kuroyanagi, J.-I., Kanai, K., Horiuchi, T., Takeshita, H.,
Achiwa, I., Kawakami, K., Yoshida, K., Kobayashi, Sh.,
and Nakamura, K., Chem. Pharm. Bull., 2011, vol. 59,
no. 3, p. 341.
4. Kozachenko, A.P., Shablykin, O.V., Vasilenko, A.N.,
and Brovarets, V.S., Russ. J. Gen. Chem., 2010, vol. 80,
no. 1, p. 127.
5-[(Morpholine-4-yl)carbonyl]-3-(2-phenylethyl)-
imidazoline-2,4-dione (VIb). Yield 86%, mp 127–129°С.
IR spectrum, ν, cm–1: 1631 (С=О), 1711 (С=О), 1771
1
(С=О), 3162–3222 (NH). Н NMR spectrum, δ, ppm:
5. Drach, B.S., Sviridov, E.P., Kisilenko, A.A., and Kir-
2.81 br.s (2Н, СН2), 3.63–3.72 m (10Н, 4СН2,
morpholine, СН2), 5.47 s (1Н, СН), 7.19–7.28 m (5Н,
С6H5), 8.40 s (1Н, NН). 13С NMR spectrum, δС, ppm:
33.80, 40.56, 43.11, 46.49, 57.49, 66.48, 66.71, 126.87,
128.90, 129.14, 138.51, 157.38, 163.44, 169.33. Found,
%: С 60.48; Н 6.20; N 13.15. С16Н19N3О4. Calculated,
%: С 60.56; Н 6.03; N 13.24. M 317.
sanov, A.V., Zh. Org. Khim., 1973, vol. 9, no. 9, p. 1818.
6. Niraimathi, V., Suresh, A.J., and Latha, T., Eur. J.
Chem., 2011, vol. 8, no. 1, p. S392.
7. Ahirwar, M.K. and Shrivastava, S.P., Eur. J. Chem.,
2011, vol. 8, no. 2, p. 931.
8. Dockendorff, Ch., Aisiku, O., VerPlank, L., Dilks, J.R.,
Smith, D.A., Gunnink, S.F., Dowal, L., Negri, J.,
Palmer, M., MacPherson, L., Schreiber, S.L., and
Flaumenhaft, R., Med. Chem. Lett., 2012, vol. 3, no. 3,
p. 232.
9. Hirota, K., Kazaoka, K., and Sajiki, H., Bioorg. Med.
Chem., 2003, vol. 11, no. 13, p. 2715.
10. Biagi, G., Giorgi, I., Livi, O., Pacchini, F., Salerni, O.,
and Scartoni, V., J. Heterocycl. Chem., 2005, vol. 42,
no. 5, p. 743.
N,N'-Dialkylethanediamides (A, B). The correspond-
ing amine (5.5 mmol) was added to a suspension of
1.05 g (5 mmol) of compound I in 10 ml of n-butanol.
The mixture was refluxed for 3 h and then kept for
12 h at 20–25°С. The precipitate formed was filtered
off. The mother liquor was additionally refluxed for
24 h and cooled to room temperature. The precipitate
formed was washed with a small amount of water and
recrystallized from ethanol.
11. Belai, I., Tetrahedron Lett., 2003, vol. 44, no. 40, p. 7475.
12. Kurz, T. and Widyan, K., Tetrahedron Lett., 2004,
N,N'-Dibenzylethanediamide (А). Yield 5%, mp
208–210°С (213–215°С [15], 221–222°С [16]). IR
vol. 45, no. 38, p. 7049.
13. Robinson, R.P., Laird, E.R., Donahue, K.M., Lopresti-
Morrow, L.L., Mitchell, P.G., Reese, M.R., Reeves, L.M.,
1
spectrum, ν, cm–1: 1654 (С=О), 3288 (NH). Н NMR
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 83 No. 9 2013