10.1002/ejoc.201801520
European Journal of Organic Chemistry
FULL PAPER
4-Cyanobenzyl diethylcarbamodithioate (3za): The synthesis
was carried out according to the typical procedure, and the residue
was purified by flash chromatography on silica gel (petroleum
ether/ethyl acetate = 100:1) to give compound 3za (51 %) as a
yellow oil. 1H NMR (400 MHz, CDCl3): δ = 7.61 (d, J=8.0 Hz, 2H),
7.52 (d, J=8.0 Hz, 2H), 4.65 (s, 2H), 4.12-3.99 (m, 2H), 3.83-3.69
(m, 2H), 1.31 (t, J=8.00 Hz, 6H) ppm. 13C NMR (100 MHz, CDCl3):
δ = 194.0, 142.8, 132.2, 130.0, 118.8, 111.1, 50.0, 46.9, 41.0, 12.6,
11.5 ppm. HRMS (ESI) m/z [M+H]+ Calcd for C13H17N2S2 265.0828;
found 265.0826.
1.79-1.66 (m, 4H), 1.44-1.33 (m, 4H), 0.98 (t, J=8.0 Hz, 6H) ppm.
13C NMR (100 MHz, CDCl3): δ = 194.2, 147.2, 145.0, 130.1, 123.6,
55.6, 52.6, 40.7, 29.7, 29.5, 28.4, 20.1, 13.8, 13.7 ppm. HRMS (ESI)
m/z [M+H]+ Calcd for C16H25N2O2S2 341.1352; found 341.1355.
Methyl 4-(((dibutylcarbamothioyl)thio)methyl)benzoate (3zg):
The synthesis was carried out according to the typical procedure,
and the residue was purified by flash chromatography on silica gel
(petroleum ether/ethyl acetate = 100:1) to give compound 3zg
1
(74 %) as a yellow oil. H NMR (400 MHz, CDCl3): δ = 7.99 (d,
J=8.0 Hz, 2H), 7.47 (d, J=8.0 Hz, 2H), 4.63 (s, 2H), 3.98 (t, J=8.0
Hz, 2H), 3.92 (s, 3H), 3.66 (t, J=8.0 Hz, 2H), 1.78-1.64 (m, 4H),
1.43-1.30 (m, 4H), 1.01-0.92 (m, 6H) ppm. 13C NMR (100 MHz,
CDCl3): δ = 194.9, 166.8, 142.1, 129.8, 129.3, 129.2, 55.3, 52.6,
52.1, 41.6, 29.4, 28.4, 20.2, 20.1, 13.8, 13.7 ppm. HRMS (ESI) m/z
[M+H]+ Calcd for C18H28NO2S2 354.1556; found 354.1551.
Naphthalen-1-ylmethyl diethylcarbamodithioate (3zb): The
synthesis was carried out according to the typical procedure, and
the residue was purified by flash chromatography on silica gel
(petroleum ether/ethyl acetate = 100:1) to give compound 3zb
(77 %) as a white solid. m.p. 71-73 °C. 1H NMR (400 MHz, CDCl3):
δ = 8.15 (d, J=8.0 Hz, 1H), 7.90 (d, J=8.0 Hz, 1H), 7.84 (d, J=8.0 Hz,
1H), 7.67-7.51 (m, 3H), 7.45 (t, J=8.0 Hz, 1H), 5.04 (s, 2H), 4.21-
4.01 (m, 2H), 3.82-3.63 (m, 2H), 1.35 (t, J=8.0 Hz, 3H), 1.25 (t,
J=8.0 Hz, 3H) ppm. 13C NMR (100 MHz, CDCl3): δ = 195.3, 133.9,
132.0, 131.5, 128.8, 128.7, 128.3, 126.4, 126.0, 125.5, 124.1, 49.4,
46.8, 40.5, 12.5, 11.7 ppm. HRMS (ESI) m/z [M+H]+ Calcd for
C16H20NS2 290.1032; found 290.1026.
Naphthalen-1-ylmethyl dibutylcarbamodithioate (3zh): The
synthesis was carried out according to the typical procedure, and
the residue was purified by flash chromatography on silica gel
(petroleum ether/ethyl acetate = 100:1) to give compound 3zh
1
(49 %) as a yellow oil. H NMR (400 MHz, CDCl3): δ = 8.14 (d,
J=8.0 Hz, 1H), 7.99 (d, J=8.0 Hz, 1H), 7.83 (d, J=8.0 Hz, 1H), 7.65-
7.50 (m, 3H), 7.44 (t, J=8.0 Hz, 1H), 5.02 (s, 2H), 4.03 (t, J=8.0 Hz,
2H), 3.63 (t, J=8.0 Hz, 2H), 1.84-1.62 (m, 4H), 1.48-1.24 (m, 4H),
1.02 (t, J=8.0 Hz, 3H), 0.91 (t, J=8.0 Hz, 3H) ppm. 13C NMR (100
MHz, CDCl3): δ = 195.7, 133.9, 132.0, 131.5, 128.7, 128.6, 128.3,
126.4, 125.9, 125.5, 124.2, 55.0, 52.5, 40.7, 29.3, 28.5, 20.2, 20.1,
13.9, 13.7 ppm. HRMS (ESI) m/z [M+H]+ Calcd for C20H28NS2
346.1658; found 346.1661.
Benzyl dibutylcarbamodithioate (3zc): The synthesis was carried
out according to the typical procedure, and the residue was purified
by flash chromatography on silica gel (petroleum ether/ethyl acetate
= 100:1) to give compound 3zc (69 %) as a yellow oil. 1H NMR (400
MHz, CDCl3): δ = 7.42 (d, J=8.0 Hz, 2H), 7.37-7.27 (m, 3H), 4.57 (s,
2H), 3.99 (t, J=8.0 Hz, 2H), 3.67 (t, J=8.0 Hz, 2H), 1.81-1.66 (m,
4H), 1.44-1.31 (m, 4H), 1.04-0.92 (m, 6H) ppm. 13C NMR (100 MHz,
CDCl3): δ = 195.7, 136.2, 129.4, 128.6, 127.4, 55.1, 52.5, 42.4, 29.4,
28.4, 20.2, 20.1, 13.9, 13.7 ppm. HRMS (ESI) m/z [M+H]+ Calcd for
C16H26NS2 296.1501; found 296.1505.
Acknowledgements
We thank the foundation support from National Natural Science
Foundation of China (21302150), foundation of Chen-Guang
program from Hubei Association for Science and Technology,
foundation of Chutian distinguished fellow from Hubei Provincial
Department of Education, foundation of Highend Talent
Cultivation Program from Wuhan Institute of Technology. Z.-B. D.
acknowledges the Humboldt Foundation and China Scholarship
Council for a fellowship.
4-Bromobenzyl dibutylcarbamodithioate (3zd): The synthesis
was carried out according to the typical procedure, and the residue
was purified by flash chromatography on silica gel (petroleum
ether/ethyl acetate = 100:1) to give compound 3zd (83 %) as a
yellow oil. 1H NMR (400 MHz, CDCl3): δ = 7.49-7.41 (m, 2H), 7.33-
7.25 (m, 2H), 4.53 (s, 2H), 3.98 (t, J=8.00 Hz, 2H), 3.66 (t, J=8.0 Hz,
2H), 1.81-1.63 (m, 4H), 1.45-1.30 (m, 4H), 1.04-0.92 (m, 6H) ppm.
13C NMR (100 MHz, CDCl3): δ = 195.1, 135.7, 131.6, 131.0, 121.3,
55.2, 52.6, 41.3, 29.4, 28.4, 20.2, 20.1, 13.8, 13.7 ppm. HRMS (ESI)
m/z [M+H]+ Calcd for C16H25BrNS2 374.0607; found 374.0611.
Keywords: metal-free • coupling • water • dithiocarbamate •
2-Bromobenzyl dibutylcarbamodithioate (3ze): The synthesis
was carried out according to the typical procedure, and the residue
was purified by flash chromatography on silica gel (petroleum
ether/ethyl acetate = 100:1) to give compound 3ze (84 %) as a
yellow oil. 1H NMR (400 MHz, CDCl3): δ = 7.57 (t, J=8.0 Hz, 2H),
7.26 (t, J=8.00 Hz, 1H), 7.12 (t, J=8.0 Hz, 1H), 4.73 (s, 2H), 3.98 (t,
J=8.0 Hz, 2H), 3.66 (t, J=8.0 Hz, 2H), 1.79-1.64 (m, 4H), 1.45-1.29
(m, 4H), 1.04-0.89 (m, 6H) ppm. 13C NMR (100 MHz, CDCl3): δ =
195.2, 136.3, 132.8, 131.6, 129.1, 127.6, 125.0, 55.2, 52.6, 42.3,
29.4, 28.4, 20.2, 20.1, 13.9, 13.8 ppm. HRMS (ESI) m/z [M+H]+
Calcd for C16H25BrNS2 374.0607; found 374.0609.
synthesis
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4-Nitrobenzyl dibutylcarbamodithioate (3zf): The synthesis was
carried out according to the typical procedure, and the residue was
purified by flash chromatography on silica gel (petroleum ether/ethyl
acetate = 100:1) to give compound 3zf (87 %) as a yellow oil. 1H
NMR (400 MHz, CDCl3): δ = 8.18 (d, J=8.0 Hz, 2H), 7.58 (d, J=8.0
Hz, 2H), 4.70 (s, 2H), 3.98 (t, J=8.0 Hz, 2H), 3.67 (d, J=8.0 Hz, 2H),
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