Lin et al.
5
CDCl ): δ=21.23, 21.98, 24.54, 25.32, 32.89, 49.94, 124.82, Declaration of conflicting interests
3
1
1
(
2
29.64, 140.46, 143.46, 165.04; IR (KBr) v: 1657cm−
The author(s) declared no potential conflicts of interest with
respect to the research, authorship, and/or publication of this
article.
C=O); ESI-HRMS m/z [M+H]+ calcd for C H NOS:
16
24
78.1573; found: 278.1578.
S-4-methoxyphenyl cyclohexylcarbamothioate (3ea):
7
White solid; yield 84%; m.p.: 149–151°C (lit. 148– Funding
1
1
3
2
(
(
50°C); H NMR (500MHz, CDCl ): δ=1.05–1.15 (m,
3
The author(s) disclosed receipt of the following financial sup-
port for the research, authorship, and/or publication of this arti-
H), 1.27–1.35 (m, 2H), 1.54–1.67 (m, 3H), 1.84–1.90 (m,
H), 3.71–3.73 (m, 1H), 3.84 (s, 3H), 5.16 (br s, 1H), 6.94 cle: This project was supported by the National Natural Science
d, J=8.9Hz, 2H), 7.47 (d, J=8.9Hz, 2H); C NMR Foundation of China (No. 21772035), the Natural Science
1
3
125MHz, CDCl ): δ=24.60, 25.36, 32.89, 50.36, 55.45, Foundation of Hunan Province, China (No. 2016JJ3050), the
3
Scientific Research Fund of Hunan Provincial Education
1
1
15.09, 119.48, 137.27, 160.85, 165.96; IR (KBr) v:
−
1
+
Department (No. 18A344), the Scientific Research Foundation
of Hunan Institute of Engineering (XJ1707), and the Open
Foundation of Key Laboratory of Environmental Catalysis &
Waste Recycling, Hunan Institute of Engineering (2018KF10).
649cm (C=O); ESI-HRMS m/z [M+H] calcd for
C H NO S: 266.1209; found: 266.1215.
1
4
20
2
S-4-(trifluoromethoxy)phenyl cyclohexylcarbamothio-
ate (3fa): White solid; yield 90%; m.p.: 134–136°C; H
1
NMR (500MHz, CDCl ): δ=1.09–1.21 (m, 3H), 1.29–1.34
3
ORCID iD
(
(
m, 2H), 1.57–1.69 (m, 3H), 189–1.96 (m, 2H), 3.69–3.77
Zhengjun Fang
m, 1H), 5.26 (br s, 1H), 7.36 (d, J=8.5Hz, 2H), 7.55 (d,
1
3
J=8.0Hz, 2H); C NMR (125MHz, CDCl ): δ=24.67,
2
1
HRMS m/z [M+H] calcd for C H F NOS: 304.0977;
found: 304.0980.
3
References
5.33, 32.95 50.92, 120.35 (q, J=258Hz), 121.45, 127.19,
−
1
1. Dai CN, Zhang J, Huang CP, et al. Chem Rev 2017; 117:
36.84, 149.95, 163.92; IR (KBr) v: 1649cm (C=O); ESI-
+
6929.
1
4
17 3
2
3
4
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. Zeng Q, Ren DM, Huang YL, et al. J Chem Res 2018; 42:
S-4-fluorophenyl cyclohexylcarbamothioate (3ga):
1
White solid; yield 92%; m.p.: 146–148°C; H NMR
3
71.
(
500MHz, CDCl ): δ=1.08–1.22 (m, 3H), 1.30–1.36 (m,
3
5
6
. Ren DM, Tng Y, Yu XY, et al. J Chem Res 2018; 42: 631.
. Ren DM, Hu XL, Huang YL, et al. J Chem Res 2018; 42:
2
1
2
5
1
H), 1.58–1.69 (m, 3H), 1.90–1.94 (m, 2H), 3.70–3.78 (m,
H), 5.21 (br s, 1H), 7.23 (d, J=8.5Hz, 2H), 7.50–7.56 (m,
4
53.
1
3
H); C NMR (125MHz, CDCl ): δ=24.66, 25.34, 32.95,
7. Pathare RS, Patil V, Kaur H, et al. Org Biomol Chem 2018;
3
0.73, 116.54 (d, J=22Hz), 123.96, 137.57 (d, J=8.6Hz),
63.50 (d, J=250Hz), 164.63; IR (KBr) v: 1654cm
C=O); ESI-HRMS m/z [M+H] calcd for C H FNOS:
16: 6885.
−1
8. Goel A, Mazur SJ, Fattah RJ, et al. Bioorg Med Chem Lett
+
2002; 12: 767.
(
2
1
3
17
9
. Bowden K and Chana RS. J Chem Soc Perkin T 2 1990; 12:
163.
54.1009; found: 254.1005.
S-4-chlorophenyl cyclohexylcarbamothioate (3ha):
2
1
1
1
0. Wood TF and Gardner JH. J Am Chem Soc 1941; 63: 2741.
1. Erian AW and Sherif SM. Tetrahedron: 1999; 55: 7957.
2. Mizuno T, Nishiguchi I, Okushi T, et al. Tetrahedron Lett
7
White solid; yield 85%; m.p.: 141–143°C (lit. 140–
1
1
3
2
2
42°C); H NMR (500MHz, CDCl ): δ=1.08–1.20 (m,
3
H), 1.27–1.38 (m, 2H), 1.54–1.73 (m, 3H), 1.88–1.95 (m,
1
991; 32: 6867.
H), 3.68–3.77 (m, 1H), 5.20 (br s, 1H), 7.37 (d, J=8.5Hz,
1
3. Chen YS, Schuphan I and Casida JE. J Agr Food Chem
1
3
H), 7.46 (d, J=8.5Hz, 2H); C NMR (125MHz, CDCl ):
3
1979; 27: 709.
δ=24.68, 25.34, 32.96, 50.84, 127.14, 129.46, 135.82, 14. Tilles H. J Am Chem Soc 1959; 81: 714.
−
1
1
36.54, 164.06; IR (KBr) v: 1648cm (C=O); ESI-HRMS 15. Padiya KJ, Gavade S, Kardile B, et al. Org Lett 2012; 14:
+
m/z [M+H] calcd for C H ClNOS: 270.0714; found:
70.0719.
S-4-bromophenyl cyclohexylcarbamothioate (3ia): White
solid; yield 79%; m.p.: 142–144°C (lit. 141–143°C); H
NMR (500MHz, CDCl ): δ=1.05–1.22 (m, 3H), 1.27–1.38
m, 2H), 1.55–1.71 (m, 3H), 1.88–1.95 (m, 2H), 3.68–3.78
2814.
1
3
17
1
1
6. Wei W, Bao P, Yue H, et al. Org Lett 2018; 20: 5291.
7. Mampuys P, Zhu Y, Sergeyev S, et al. Org Lett 2016; 18:
2808.
2
23
1
1
8. Xie LY, Peng S, Tan JX, et al. ACS Sustain Chem Eng 2018;
3
6
: 16976.
(
(
1
2
9. Xie LY, Li YJ, Qu J, et al. Green Chem 2017; 19: 5642.
0. Wu C, Lu LH, Peng AZ, et al. Green Chem 2018; 20: 3683.
m, 1H), 5.20 (br s, 1H), 7.39 (d, J=8.0Hz, 2H), 7.52 (d,
13
J=8.0Hz, 2H); C NMR (125MHz, CDCl ): δ=24.69,
3
21. Xie LY, Peng S, Liu F, et al. Adv Synth Catal 2018; 360:
259.
IR (KBr) v: 1653cm (C=O); ESI-HRMS m/z [M+H]+ 22. Zhao WN and Zhou AH. Chem Cat Chem 2015; 7: 3464.
calcd for C H BrNOS: 314.0209; found: 314.0215.
23. Jeong KS. B Korean Chem Soc 2008; 29: 1621.
2
5.34, 32.97, 50.86, 124.10, 127.77, 132.42, 136.75, 163.89;
4
−1
13
17