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PRISHCHENKO et al.
1.05–1.25 m (12H, CH3), 2.40–2.55 m (2H, CH2),
3.80–4.05 m (8H, CH2O), 7.05–7.76 m (5H, C6H5),
8.25–8.28 m (1H, NH). 13C NMR spectrum, δC, ppm:
15.85–16.10 m (CH3), 35.05–38.50 m (C2), 62.90–
3.45–3.55 m (2H, CH2O), 7.78 d (1H, NH, 3JPH 6.0 Hz).
1
13C NMR spectrum, δC, ppm: 11.86 d (CH3P, JPC
92.3 Hz), 15.60 (CH3), 25.32 (CH3CO), 37.17 d
1
2
(PCH2, JPC 103.3 Hz), 59.70 d (CH2O, JPC 6.6 Hz),
171.80 (C=O). 31P NMR spectrum: δP 49.86 ppm. The
1
1
65.85 m (CH2O), 69.15 d.d (C1, JP C
1
101.4, JP C
2
145.3 Hz), 126.55–133.85 m (Ph), 161.68 d.d (C3, 2JP C
1
second isomer, content 35%. H NMR spectrum, δ,
ppm: 0.95 d (3H, CH3P, JPH 14.4 Hz), 0.73 t (3H,
CH3, JHH 6.8 Hz), 1.40 s (3H, CH3CO), 2.87–3.96 m
1
3
2
11.2, JP C
2
21.6 Hz). 31P NMR spectrum, δP, ppm:
13.08 d (P2, JPP 27.4 Hz), 37.18 d (P1, JPP 27.4 Hz).
2
2
3
1
The second isomer, content 35%. H NMR spectrum,
(2H, PCH2), 3.45–3.55 m (2H, CH2O), 7.78 d (1H,
3
δ, ppm: 1.05–1.25 m (9H, CH3), 2.40–2.55 m (2H,
C2H2), 3.80–4.05 m (6H, CH2O), 7.05–7.76 m (5H,
C6H5), 8.25–8.28 m (1H, NH). 13C NMR spectrum, δC,
ppm: 15.85–16.10 m (CH3), 35.05–38.50 m (C2),
NH, JPH 5.6 Hz). 13C NMR spectrum, δC, ppm: 13.43
1
d (CH3P, JPC 91.2 Hz), 15.55 (CH3), 21.44 (CH3CO),
1
2
42.74 d (PCH2, JPC 102.6 Hz), 59.92 d (CH2O, JPC
6.6 Hz), 169.45 d (C=O, JPC 2.9 Hz). 31P NMR spec-
3
1
1
62.90–65.85 m (CH2O), 68.96 d.d (C1, JP C
1
102.1, JP C
2
trum: δP 47.76 ppm. Found, %: C 40.03; H 7.72.
C6H14NO3P. Calculated, %: C 40.23; H 7.88.
146.0 Hz), 126.55–133.85 m (Ph), 160.76 d.d (C3, 2JP C
1
13.6, JP C
23.1 Hz). 31P NMR spectrum, δP, ppm:
2
3
14.67 d (P2, 2JPP 15.9 Hz), 38.78 d (P1, 2JPP 15.9 Hz).
O,O-Diethyl [(N-acetyl-N-methylamino)(phenyl)-
methyl]phosphinate (5). Yield 88%, bp 198°C
(2 mmHg). The first isomer, content 80%.1H NMR
spectrum, δ, ppm: 0.71 t (3H, CH3, 3JHH 6.8 Hz), 0.87 t
O,O-Diethyl (N-acetyl-N-ethylaminomethyl)phos-
phonate (3). Yield 85%, bp 133°C (0.5 mmHg). The
3
1
(3H, CH3, JHH 7.2 Hz), 1.68 s (3H, CH3CO), 2.60 s
first isomer, content 75%. H NMR spectrum, δ, ppm:
3
3
(3H, CH3N), 3.50–3.85 m (4H, CH2O), 5.99 d (1H,
0.69 t (3H, CH3, JHH 7.2 Hz), 0.79 t (6H, CH3, JHH
2
PCH, JPH 22.8 Hz), 6.85–7.35 m (5H, C6H5). 13C
3
6.8 Hz), 1.60 s (3H, CH3CO), 3.02 t (2H, CH2N, JHH
3
7.2 Hz), 3.31 d (2H, PCH2, 2JPH 11.6 Hz), 3.50–3.75 m
(4H, CH2O). 13C NMR spectrum, δC, ppm: 12.19
NMR spectrum, δC, ppm: 15.36 d (CH3, JPC 5.5 Hz),
3
15.62 d (CH3, JPC 5.5 Hz), 20.88 (CH3CO), 32.35
1
3
(CH3N), 51.63 d (PCH, JPC 157.5 Hz), 61.51 d
(CH3), 15.40 d (CH3, JPC 6.2 Hz), 19.86 (CH3CO),
38.81 d (PC, JPC 156.4 Hz), 42.87 (CH2N), 61.21 d
(CH2O, JPC 6.2 Hz), 168.92 br.s (C=O). 31P NMR
2
(CH2O, JPC 1.5 Hz), 61.69 br.s (CH2O), 127.42 (Cp),
1
3
127.83 (Cm), 128.87 d (Cо, JPC 8.8 Hz), 132.93 d
2
2
3
(Cipsо, JPC 4.8 Hz), 169.88 (C=O, JPC 5.2 Hz). 31P
spectrum: δP 22.37 ppm. The second isomer, content
25%. 1H NMR spectrum, δ, ppm: 0.58 t (3H, CH3, 3JHH
NMR spectrum: δP 20.57 ppm. The second isomer,
1
content 20%. H NMR spectrum, δ, ppm: 0.71 t (3H,
3
7.2 Hz), 0.82 t (6H, CH3, JHH 7.2 Hz), 1.63 s (3H,
CH3, 3JHH 6.8 Hz), 0.87 t (3H, CH3, 3JHH 7.2 Hz), 1.85
s (3H, CH3CO), 2.53 s (3H, CH3N), 4.83 d (1H, PCH,
2JPH 23.6 Hz), 3.50–3.85 m (4H, CH2O), 6.85–7.35 m
(5H, C6H5). 13C NMR spectrum, δC, ppm: 15.36 d
3
CH3CO), 3.03 t (2H, CH2N, JHH 7.2 Hz), 3.17 d (2H,
2
PCH2, JPH 10.0 Hz), 3.50–3.75 m (4H, CH2O). 13C
NMR spectrum, δC, ppm: 11.08 (CH3), 15.52 d (CH3,
3JPC 5.5 Hz), 20.86 (CH3CO), 40.65 (CH2N), 43.34 d
3
3
(CH3, JPC 5.5 Hz), 15.62 d (CH3, JPC 5.5 Hz), 20.00
(CH3CO), 29.79 (CH3N), 58.52 d (PCH, 1JPC 157.5 Hz),
61.51 d (CH2O), 61.69 br.s (CH2O), 127.42 (Cp),
1
2
(PC, JPC 159.0 Hz), 61.53 d (CH2O, JPC 7.0 Hz),
169.33 br.s (C=O). 31P NMR spectrum: δP 21.14 ppm.
Found, %: C 45.52; H 8.42. C9H20NO4P. Calculated,
%: C 45.57; H 8.50.
3
128.01 (Cm), 128.24 d (Cо, JPC 8.1 Hz), 132.52 d
(Cipso, 2JPC 4.4 Hz), 171.58 (C=O). 31P NMR spectrum:
δP 20.07 ppm. Physicochemical characteristics of phos-
phonate 5 matched the data described by us earlier [4, 5].
O-Ethyl (methyl)(N-acetylaminomethyl)phosphi-
nate (4). Yield 83%, bp 157°C (1 mmHg). The first
isomer, content 65%. 1H NMR spectrum, δ, ppm: 0.71
NMR spectra (CDCl3) were obtained on a Bruker
Avance 400 spectrometer using TMS (1H and 13C) or
85% solution of H3PO4 in D2O (31P NMR) as a reference.
3
2
t (3H, CH3, JHH 7.2 Hz), 0.90 d (3H, CH3P, JPH
14.0 Hz), 1.89 s (CH3CO), 2.87–3.96 m (2H, PCH2),
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 85 No. 10 2015