QUATERNARY AMMONIUM SALTS BASED ON 2,3-DICHLOROPROP-1-ENE
451
under reduced pressure. Yield 14.3 g (68%), bp 56–
6 h at 60°C, the organic phase was separated, and
crystals of quaternary salt III separated in one or two
days at room temperature. Yield 58.0 g (80%), decom-
2
0
–1
5
1
8°C (30 mm), nD = 1.4437. IR spectrum, ν, cm :
648 (C=C), 1250, 1050 (C–N). H NMR spectrum, δ,
1
–
1
ppm: 0.99 t (6H, CH , J = 6.9 Hz), 2.55 q (4H, CH ,
poses at 165°C without melting. IR spectrum, ν, cm :
3
2
1
J = 6.9 Hz), 3.17 s (2H, CH ), 5.35 d (2H, =CH , J =
3080, 2975, 1648 (C=C), 1030, 1230 (C–N). H NMR
2
2
1
3
8
4
2.7 Hz). C NMR spectrum, δ , ppm: 12.55 (CH ),
spectrum, δ, ppm: 3.41 s (6H, CH ), 4.70 s (4H, CH ),
C
3
3
2
1
3
7.97 (CH ), 60.66 (CH ), 113.88 (=CH ), 141.69
6.18 d (4H, =CH , J = 96.7 Hz). C NMR spectrum,
2
2
2
2
(
=CCl). Found, %: C 56.60; H 10.10; Cl 25.00; N 9.90.
δ , ppm: 47.33 (CH ), 66.51 (CH ), 125.33 (=CCl),
C
3
2
C H ClN. Calculated, %: C 56.95; H 9.49; Cl 24.07;
126.12 (=CH ). Found, %: C 41.68; H 6.60; Cl 44.34;
7
14
2
N 9.49.
N 6.84. C
H14Cl N. Calculated, %: C 41.65; H 6.07;
8 3
Cl 46.2; N 6.08.
(
2-Chloroprop-2-en-1-yl)triethylammonium
bromide (II). A solution of 20 g of ethyl bromide in
nitromethane was added under stirring to a mixture of
The elemental compositions were determined on
a Thermo Finnigan Flash EA 1112 Series analyzer. The
IR spectra were recorded in KBr on a Specord 75IR
1
0 g of compound I and 18 ml of nitromethane. After
1
13
cooling, the precipitate was filtered off and dried. Yield
spectrometer. The
H and C NMR spectra were meas-
–
1
1
3
2 g (80%), mp 168–170°C. IR spectrum, ν, cm :
ured on a Varian VXR-500S spectrometer from solu-
tions in C D OD using hexamethyldisiloxane as in-
1
050, 2875, 1618 (C=C), 1280 (C–N). H NMR spec-
2
5
trum, δ, ppm: 1.41 (6H, CH , J = 7.1 Hz), 3.55 q (4H,
3
ternal reference.
CH , J = 7.1 Hz), 4.45 s (2H, CH N), 6.08 (2H, =CH ,
2
2
2
This study was performed under financial support
by the Russian Foundation for Basic Research (project
nos. 09-08-00411, 09-08-00418).
1
3
J = 109.6 Hz). C NMR spectrum, δ , ppm: 8.76
C
(
CH ), 54.93 (CH ), 62.91 (CH ), 129.58 (=CH ),
3 2 2 2
1
30.02 (=CCl). Found, %: C 43.09; H 8.34; Br 31.21;
Cl 13.85; N 5.70. C H BrClN. Calculated, %:
C 42.12; H 7.46; Br 31.14; Cl 13.82; N 5.46.
9
19
REFERENCES
Bis(2-chloroprop-2-en-1-yl)dimethylammonium
chloride (III). Freshly distilled 2,3-dichloroprop-1-
ene, 55 ml (0.5 mol), and 50% aqueous sodium hy-
droxide, 50 g (0.625 mol), were added under vigorous
stirring over a period of 20 min to 68.2 g (0.5 mol) of
1. Voronkov, M.G., Tatarova, L.A., Trofimova, K.S., Ver-
khozina, E.I., and Khaliullin, A.K., Khim. Inter. Ustoich.
Razv., 2001, vol. 9, no. 3, p. 393.
2. Agaev, N.M., Maksimov, Kh.A., and Sharifov, G.S.,
Azerb. Neft. Khoz., 2005, p. 46.
3
3% aqueous dimethylamine, maintaining the tempera-
3. Spravochnik khimika (Chemist’s Handbook), Pote-
ture below 40°C. The mixture was then heated for 4–
khin, A.A., Ed., Leningrad: Khimiya, 1984, p. 329.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 46 No. 3 2010