HASRATYAN et al.
960
bp 130°C (1 mm), n2D0 = 1.5000; published data:
bp 120–122°C (0.02 mm) [9], nD28 = 1.5055 [10]. IR
REFERENCES
1
spectrum: ν 1650 cm–1 (C=O). H NMR spectrum, δ,
1. Zakaryan, G.B., Hayotsyan, S.S., Attaryan, H.S., and
Hasratyan, G.V., Russ. J. Gen. Chem., 2015, vol. 85,
p. 1773.
ppm: 1.48–1.63 m (12H, CH2), 3.03–3.14 m [8H,
N(CH2)2]. 13C NMR spectrum, δC, ppm: 24.2, 25.1,
47.1, 163.2.
2. Zakaryan, G.B., Hayotsyan, S.S., Attaryan, H.S., and
Hasratyan, G.V., Russ. J. Gen. Chem., 2016, vol. 86,
p. 1195.
N,N,N′,N′-Tetramethylurea (7) was synthesized
from 50 mL of 40% aqueous dimethylamine. Yield
2.3 g (40%), bp 75–77°C (15 mm), nD20 = 1.4500;
3. Zakaryan, G.B., Hayotsyan, S.S., Ayvazyan, A.G.,
Tamazyan, R.A., Panosyan, H.G., Danagulyan, G.G., and
Attaryan, H.S., Chem. Heterocycl. Compd., 2016,
vol. 52, no. 4, p. 253.
published data: bp 63.5–64°C (12 mm) [11], nD20
=
1.4495 [12]. IR spectrum: ν 1670 cm–1 (C=O).
1H NMR spectrum, δ, ppm: 2.74 s (12H, CH3).
13C NMR spectrum, δC, ppm: 38.9, 95.46.
4. Graefe, J., Frölich, I., and Mühlstädt, M., Z. Chem.,
1974, vol. 14, p. 434.
N,N,N′,N′-Tetraethylurea (8) was synthesized
from 50 mL of 25% aqueous diethylamine. Yield 2.1 g
(25%), bp 70°C (1 mm), nD20 = 1.4450; published data:
bp 90–91°C (9 mm) [13], nD25 = 1.4448 [14]. IR spec-
5. Makosza, M. and Kacprowicz, A., Rocz. Chem., 1975,
vol. 49, p. 1627.
6. Gol’dberg, Yu.Sh. and Shimanovskaya, M.V., Zh. Org.
Khim., 1982, vol. 18, p. 2036.
1
trum: ν 1675 cm–1 (C=O). H NMR spectrum, δ, ppm:
7. Shastri, L.A., Shastri, S.L., Bathula, Ch.D., Basana-
gouda, M., and Kulkazni, M.V., Synth. Commun., 2011,
vol. 41, p. 476.
1.07 m (12H, CH3, J = 7.1 Hz), 3.09 q (8H, CH2,
J = 7.1 Hz). 13C NMR spectrum, δC, ppm: 12.71,
41.54, 163.17.
8. Mizuno, T., Nakai, T., and Mihara, N., Synthesis, 2010,
The IR spectra were recorded on a Thermo Nicolet
Nexus spectrometer from samples dispersed in mineral
no. 24, p. 4251.
9. Kantlehner, W., Maier, T., Loffler, W., and Kapassa-
1
oil. The H and 13C NMR spectra were measured at
kalidis, J.J., Justus Liebigs Ann. Chem., 1982, p. 507.
300 K on a Varian Mercury-300VX spectrometer at
300 and 75 MHz, respectively, using DMSO-d6–CCl4
(1 :3) as solvent and tetramethylsilane as internal
standard. The elemental analyses were obtained on
a Eurovector EA 3000 analyzer.
10. Fenton, D.M., US Patent no. 3277061, 1966.
11. Paul, R.C., Johar, S.P., Banalt, J.S., and Narula, S.P.,
J. Phys. Chem., 1976, vol. 80, no. 4, p. 351.
12. Lawson, J.K. and Croom, J.A.T., J. Org. Chem., 1963,
vol. 28, p. 232.
This study was performed under financial support
by the State Science Committee of the Ministry of
Education and Science of the Republic of Armenia
(research project no. 15 T-1 D348).
13. Kirkwood, M.W. and Wright, G.F., Can. J. Chem., 1957,
vol. 35, p. 527.
14. Rosenfarb, J., Huffman, H.L.J., and Caruso, J.A.,
J. Chem. Eng. Data, 1976, vol. 21, no. 2, p. 150.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 54 No. 6 2018