Ar
O
O
Me
Et3N,
Me2CO
NC
O
CN
NC
Ar
NC
NH2
N
N
+
N
H
O
+
Me
Et3NH
3
2
1
1, 3 Ar = 2-ClC6H4
1
13
The IR spectra were obtained on an IKS-29 spectrometer in nujol mulls. The H and C NMR spectra
were taken on a Bruker DRX-500 spectrometer at 500 and 125 MHz, respectively, in DMSO-d6 with TMS as
internal standard. The elemental analysis was carried out on a Perkin-Elmer CHN analyzer.
Triethylammonium 4-(2-Chlorophenyl)-3,5-dicyano-6-oxo-1,4,5,6-tetrahydropyridin-2-olate (1).
Triethylamine
dried
over
KOH
(1.2 ml,
8.6 mmol)
was
added
to
a
mixture
of
(E)-3-(2-chlorophenyl)-2-cyanoacrylamide 3 (1.20 g, 5.8 mmol) and cyanoacetylpyrazole 2 (1.10 g, 6.7 mmol)
in warm acetone (15 ml). The flask with the reaction mixture was left at 10–15°C for 72–120 h. The white
crystalline precipitate was filtered off and washed with cold acetone and ether to give 1.64 g (76%) pure salt 1;
mp >250°C; Rf 0.69 (acetone–hexane, 1:1). Attention! This compound causes sneezing. IR spectrum, , cm–1:
1
3170 (NH), 2255 (unconj. C≡N), 2175 (C≡N), 1695 (C=O). H NMR spectrum, , ppm (J, Hz): 1.16 (9H, t,
3
3J = 7.1, 3CH3CH2); 3.05 (6H, q, J = 7.1, 3CH3CH2); 4.19–4.79 (2H, m, superposition of signals of
diastereomeric H-4 and H-5); 7.27–7.50 (4H, m, H Ar); 9.71 (1H, br. s, NH). The signals of the NH+ proton are
not seen due to deuterium exchange. 13C NMR spectrum, , ppm: 9.34, 37.30, 41.78, 46.31, 128.07, 128.17,
129.10, 129.32, 129.75, 129.97, 133.13, 133.70, 138.47, 140.50, 164.32, 164.51. Found, %: C 61.14; H 6.24;
N 14.90. C19H23ClN4O2. Calculated, %: C 60.88; H, 6.18; N 14.95.
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