66
TOLSTIKOVA et al.
a mixture of 0.40 g (2.05 mmol) of compound 1 and
.15 g (1.00 mmol) of adipic acid (6). The mixture was
Reaction of N-sulfinyltrifluoromethanesulfon-
amide with succinic acid. Succinic acid (4), 0.12 g
(1.00 mmol), and thionyl chloride, 0.1 mL, were added
to 0.40 g (2.05 mmol) of compound 1. The mixture was
stirred for 20 min at room temperature and for 20 min
at 45°C, cooled, and evaporated. The residue was
dissolved in a small volume of acetone, and the product
(succinic anhydride) was precipitated with hexane,
0
stirred at 75–80°C for 30 min until complete crystal-
lization and washed with chloroform, and the product
was reprecipitated from acetone with hexane and dried
under reduced pressure. Yield 0.22 g (54%), mp 191–
–
1
1
1
92°C. IR spectrum (film), ν, cm : 3172, 1734, 1457,
1
398, 1232, 1205, 1140, 1088, 876, 609. H NMR
1
spectrum (CD CN), δ, ppm: 1.62–1.65 m (4H, CH ),
filtered off, and dried. Yield 0.065 g (65%). H NMR
3
2
1
3
2
.44–2.47 m (4H, CH ), 6.62 br.s (2H, NH). C NMR
spectrum (CDCl ), δ, ppm: 3.01 s (CH ) (3.02 ppm
2
3
2
1
3
spectrum (CD CN), δ , ppm: 23.72 (CH ), 36.89
[6]). C NMR spectrum (CDCl ), δ , ppm: 28.34
3
C
2
3 C
1
(
CH ), 120.28 q (CF , J = 320.8 Hz), 171.25 (C=O).
F NMR spectrum (CD CN): δ –77.42 ppm. Found,
(CH ), 170.67 (C=O) (28.38, 170.65 ppm [6]).
2
3
CF
2
1
9
3
F
Reaction of N-sulfinyltrifluoromethanesulfon-
amide with 4-nitrophthalic acid. 4-Nitrophthalic acid
%
: C 23.40; H 2.44; F 27.34; N 6.78; S 15.23.
C H F N O S . Calculated, %: C 23.53; H 2.47;
8
10
6
2
6 2
(8), 0.21 g (1.00 mmol), and thionyl chloride, 0.1 mL,
F 27.92; N 6.86; S 15.71.
were added to 0.40 g (2.05 mmol) of compound 1. The
mixture was stirred for 40 min at 90–95°C, cooled, and
evaporated under reduced pressure. The residue was
dissolved in a small amount of acetone, and the product
(5-nitro-2-benzofuran-1,3-dione) was precipitated with
hexane, filtered off, washed with diethyl ether, and
dried. Yield 0.072 g (37%). IR spectrum (film), ν,
N,N′-Bis(trifluoromethanesulfonyl)decanedi-
amide (14). Thionyl chloride, 0.1 mL, was added to
a mixture of 0.45 g (2.30 mmol) of compound 1 and
0
.20 g (1.00 mmol) of sebacic acid (7). The mixture
was stirred at 50–55°C for 10 min until complete
crystallization, and the product was reprecipitated from
acetone with hexane, washed with diethyl ether, and
dried under reduced pressure. Yield 0.12 g (26%),
–
1
cm : 3111, 1852, 1791, 1545, 1348, 1258, 1126, 929,
1
899, 710. H NMR spectrum (CD CN), δ, ppm: 8.19 d
3
–
1
mp 192–195°C. IR spectrum, KBr, ν, cm : 3136,
(1H, 7-H, J = 8.4 Hz), 8.59 d (1H, 6-H, J = 8.4 Hz),
8.61 s (1H, 4-H); published data [6]: δ, ppm: 8.28 d
(J = 8.2 Hz), 8.79 d.d (J = 8.2, 1.8 Hz), 8.86 d (J =
2
6
931, 2858, 1728, 1470, 1398, 1213, 1135, 1087, 881,
1
13. H NMR spectrum (DMSO-d ), δ, ppm: 1.24 s
6
1
3
(
8H, CH ), 1.51 br.t (4H, CH , J = 7.2 Hz), 2.37 t (4H,
1.4 Hz). C NMR spectrum (CD CN), δ , ppm:
2
2
3 C
1
3
CH , J = 7.2 Hz), 9.08 br.s (2H, NH). C NMR
121.65, 127.99, 132.19, 133.91, 136.80, 153.90,
162.22, 162.49.
2
spectrum (DMSO-d ), δ , ppm: 23.84 (CH ), 28.03
6
C
2
(
CH ), 28.34 (CH ), 36.35 (CH ), 119.21 q (CF ,
2 2 2 3
The antimicrobial activity of compounds 5, 6, 12,
3, and 16 and salicylic acid against Bacillus subtilis
B-406, Enterococcus durans B-603, Penicillium
citreoviride F-1777, and Escherichia coli B-1238
provided by the All-Russian Collection of Micro-
organisms) was assayed by standard disk diffusion
method [8]. The compounds to be tested were dissolved
in water to concentrations of 15 to 1000 μg/mL. The
test cultures were grown on potato agar (B. subtilis),
modified medium (no. 75 VKM) for lactic acid bacteria
with addition of Twin-80 (E. durans), beef extract agar
(E. coli), or wort agar (P. citreoviride). The results were
evaluated by the appearance of bacterial growth inhibi-
tion zone. Only minimum inhibitory concentrations
were determined (Table 2).
1
19
JCF = 320.5 Hz), 172.21 (C=O). F NMR spectrum
DMSO-d ): δ –76.35 ppm. Found, %: C 31.14;
1
(
6
F
H 3.94; N 5.96; S 13.11. C H F N O S . Calculat-
1
2
18
6
2
6 2
ed, %: C 31.04; H 3.91; N 6.03; S 13.81.
-Methyl-N-(trifluoromethanesulfonyl)prop-
-enamide (15). Methacrylic acid (11), 0.17 g
2.00 mmol), and thionyl chloride, 0.1 mL, were added
(
2
2
(
to 0.58 g (3.00 mmol) of compound 1. The mixture was
stirred at room temperature for 3 h and at –5°C for
1
dryness. Yield 0.68 g (82%). IR spectrum (film), ν,
cm : 3384, 3276, 1715, 1445, 1382, 1202, 1134, 1089,
8
6 h, washed with chloroform, and evaporated to
–1
1
61, 603. H NMR spectrum (CDCl ), δ, ppm: 1.96 s
3
(3H, CH ), 5.80 s (1H, =CH ), 5.97 s (1H, =CHtrans),
3 cis
1
3
8
.93 br.s (1H, NH). C NMR spectrum (CDCl ), δ ,
3 C
1
ppm: 17.81 (CH ), 119.10 q (CF , J = 320.8 Hz),
1
ACKNOWLEDGMENTS
3
3
CF
1
9
26.10 (CH =), 137.48, 164.17 (C=O). F NMR spec-
2
trum (CDCl ): δ –75.46 ppm. Found, %: C 27.42;
This study was performed using the equipment of the
Baikal Joint Center (Siberian Branch, Russian Academy of
Sciences).
3
F
H 2.59; N 6.88; S 17.204. C H F NO S. Calculat-
5
6
3
3
ed, %: C 27.65; H 2.78; N 6.45; S 14.77.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 56 No. 1 2020