1,3,4-THIAZAPHOSPHOL-2-INES CONTAINING ACETAL GROUPS
2275
(5H, Ph). 31P NMR spectrum (acetone-d6 : C6H6 = 1:1],
δP, ppm: 115.70. Found, %: C 44.45; H 5.56; N 7.43; P
8.41; S 17.97. C13H19N2O3PS2. Calculated, %: C 45.06;
H 5.54; N 8.09; P 8.94; S 18.51.
(1H, NH). 31P NMR spectrum (acetone-d6), δP, ppm:
116.67. Found, %: C 49.00; H 6.18; N 7.07; P 8.33; S
16.49. C16H25N2O3PS2. Calculated, %: C 49.46; H
6.50; N 7.21; P 7.97; S 16.51.
The IR spectra were registered on a UR-20 spec-
2-[N-(O,O-Dimethyl)ethyl]amino-4-phenoxy-4-thi-
oxo-1,3,4-thiazaphosphol-2-yne (IVb) was prepared
similarly from 0.59 g of aminoacetal IIb, 0.6 g of tri-
ethylamine and 1.48 g of isothiocyanate I. Yield 0.90 g
trometer in the range of 400–3600 сm–1 (mineral oil).
1
The H NMR spectra were measured on a Bruker
31
AVANCE-600 spectrometer (600 MHz). The P NMR
1
spectra were recorded on a Bruker MSL-400 spec-
trometer (162 MHz). The mass spectra were taken on a
TRACE-MS Finnigan-MAT device.
(49%), colorless viscous liquid. H NMR spectrum
[(CD3)2CO], δ, ppm: 3.34 s (3H, OCH3), 3.35 s (3H,
3
OCH3), 3.40 d (2H, NCH2, JHH 3.15 Hz), 3.53 d. d
2
2
(1H, PCH2, JPH 3.60, JHH 13.05 Hz), 3.60 m (2H,
2
2
ACKNOWLEDGMENTS
NCH2), 3.90 d. d (1H, PCH2, JPH = JHH 13.05 Hz),
4.53 t (1H, OCH, 3JHH 4.95 Hz), 7.18-7.23 m (5H, Ph),
7.82 s (1H, NH). 31P NMR spectrum (acetone-d6), δP,
ppm: 117.96. Found, %: C 43.45; H 5.18; N 7.93; P
9.21. C12H17N2O3PS2. Calculated, %: C 43.35; H 5.16;
N 8.43; P 9.32.
This work was financially supported by the Russian
Foundation for Basic Research (grant no. 09-03-
00029).
REFERENCES
2-[N-(O,O-Diethyl)butyl]amino-4-phenoxy-4-thi-
oxo-1,3,4-thiazaphosphol-2-yne (IVc) was prepared
similarly from 0.94 g of aminoacetal IIc, 0.6 g of
triethylamine, and 1.54 g of isothiocyanate I. Yield
1.47 g (65%), colorless viscous liquid. 1H NMR
spectrum, [(CD3)2CO], δ, ppm: 1.07–1.20 m (6H,
CH3), 1.86–1.95 m (2H, CH2), 2.03–2.08 m (2H, CH2),
1. Kamalov, R.M., Khailova, N.A., Gazikasheva, A.A.,
Chertanova, L.F., Pudovik, M.A., and Pudovik, A.N.,
Dokl. Akad. Nauk SSSR, 1991, vol. 316, no. 6, p. 1406.
2. Khailova, N.A., Krepysheva, N.E., Saakyan, G.M.,
Bagautdinova, R.Kh., Shaimardanova, A.A., Zyabli-
kova, T.A., Azancheev, N.M., Litvinov, I.A., Gubai-
dullin, A.T., Zverev, V.V., Pudovik, M.A., and Pudo-
vik, A.N., Zh. Obshch. Khim., 2002, vol. 72, no. 7, p. 1145.
2
3.45–3.62 m (2H, NCH2), 3.60 d. d (1H, PCH2, JPH
3.76, 2JHH 13.51 Hz), 3.73–3.92 m (4H, OCH2), 3.94 d.
3. Chmutova, G.A., Zverev, V.V., Pudovik, M.A., Khai-
lova, N.A., and Pudovik, A.N., Zh. Obshch. Khim.,
2003, vol. 73, no. 11, p. 1793.
2
2
d (1H, PCH2, JPH 5.41, JHH 13.51 Hz), 5.10 t (1H,
2
OCH, JHH 4.95 Hz), 7.19–7.28 m (5H, Ph), 7.43 s
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 79 No. 10 2009