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Green Chemistry
Page 6 of 8
DOI: 10.1039/C7GC02311A
ARTICLE
Journal Name
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solid (148 mg, 90%). Mp: 209-210 °C; H NMR (400 MHz, DMSO-d6, 5-Fluoro-1,3-dihydro-benzoimidazole-2-thione 3t[28]: According to
TMS): δ (ppm) 13.61 (brs, 1H), 7.17 (s, 1H), 6.97 (s, 2H), 2.24 (s, 3H). TP, the residue was purified by flash chromatography on silica gel
13C NMR (100 MHz, DMSO-d6, TMS): δ (ppm) 179.8, 148.2, 133.5, (petroleum ether/ethyl acetate 1:1) to give the target compound 3t
128.7, 125.5, 110.1, 109.8, 20.8. HRMS (ESI): Calcd for C8H7NOS as a white solid (149 mg, 89%). Mp: 284-285 °C; 1H NMR (400 MHz,
(165.0248), found: 165.0256.
DMSO-d6, TMS): δ (ppm) 12.64 (d, J = 12.0 Hz, 2H), 7.13-7.09 (m,
1H), 6.96 (t, 2H, J = 8.0 Hz). 13C NMR (100 MHz, DMSO-d6, TMS): δ
(ppm) 169.8, 160.1 (d, 1C, J = 235 Hz), 133.2 (d, 1C, J = 13 Hz),
129.3, 110.5 (d, 1C, J = 10 Hz), 109.8 (d, 1C, J = 25 Hz), 97.4 (d, 1C, J
= 28 Hz). MS (EI): Calcd for C7H5FN2S (168.0157), found: 168.0169.
7-Methyl-benzooxazole-2-thiol 3n[35]: According to TP, the residue
was purified by flash chromatography on silica gel (petroleum
ether/ethyl acetate 3:1) to give the target compound 3n as a red
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solid (132 mg, 80%). Mp: 243-245 °C; H NMR (400 MHz, DMSO-d6,
TMS): δ (ppm) 13.69 (brs, 1H), 7.04 (t, 1H, J = 8.0 Hz), 6.92 (t, 2H, J = 5,6-Dichloro-1,3-dihydro-benzoimidazole-2-thione
8.0 Hz), 2.25 (s, 3H). 13C NMR (100 MHz, DMSO-d6, TMS): δ (ppm) According to TP, the residue was purified by flash chromatography
3u[29]
:
180.9, 147.9, 131.7, 125.9, 125.8, 120.9, 108.9, 15.2. HRMS (ESI): on silica gel (petroleum ether/ethyl acetate 1:1) to give the target
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Calcd for C8H7NOS (165.0248), found 165.0241.
compound 3u as a yellow solid (179 mg, 82%). Mp: 350-351 °C; H
NMR (400 MHz, DMSO-d6, TMS): δ (ppm) 12.81 (brs, 2H), 7.32 (s,
2H). 13C NMR (100 MHz, DMSO-d6, TMS): δ (ppm) 170.7, 132.6,
125.1, 110.9. HRMS (ESI): Calcd for C7H4Cl2N2S (219.9472), found:
217.9486.
4,5-Dihydro-oxazole-2-thiol 3o[25]: According to TP, the residue was
purified by flash chromatography on silica gel (petroleum
ether/ethyl acetate 3:1) to give the target compound 3o as a white
solid (32 mg, 31%). Mp: 99-100 °C; 1H NMR (400 MHz, DMSO-d6,
TMS): δ (ppm) 10.11 (brs, 1H), 3.88 (t, 2H, J = 8.0 Hz), 3.52 (t, 2H, J = 5-Nitro-1,3-dihydro-benzoimidazole-2-thione 3v[26]: According to
8.0 Hz). 13C NMR (100 MHz, DMSO-d6, TMS): δ (ppm) 199.4, 51.9, TP, the residue was purified by flash chromatography on silica gel
33.3. HRMS (ESI): Calcd for C3H5NOS (103.0092), found: 103.0109.
(petroleum ether/ethyl acetate 1:1) to give the target compound 3v
as a yellow solid (128 mg, 66%). Mp: 273-275 °C; 1H NMR (400 MHz,
DMSO-d6, TMS): δ (ppm) 13.08 (brs, 2H), 8.04 (d, J = 8.0 Hz, 1H),
7.85 (s, 1H), 7.26 (d, J = 8.0 Hz, 1H). 13C NMR (100 MHz, DMSO-d6,
TMS): δ (ppm) 172.2, 143.0, 137.8, 132.6, 119.3, 109.6, 105.1.
HRMS (ESI): Calcd for C7H5N3O2S (195.0102), found: 195.0121.
Oxazolo[4,5-b]pyridine-2-thiol 3p[15]: According to TP, the residue
was purified by flash chromatography on silica gel (petroleum
ether/ethyl acetate 3:1) to give the target compound 3p as a white
solid (58 mg, 38%). Mp: 238-240 °C; 1H NMR (400 MHz, DMSO-d6,
TMS): δ (ppm) 14.47 (brs, 1H), 8.21 (s, 1H), 7.86 (s, 1H), 7.25 (s, 1H).
13C NMR (100 MHz, DMSO-d6, TMS): δ (ppm) 181.8, 147.5, 144.6, 2-Thioxo-2,3-dihydro-1H-benzoimidazole-5-carbonitrile
3w[30]
:
142.1, 119.5, 117.5. HRMS (ESI): Calcd for C6H4N2OS (152.0044), According to TP, the residue was purified by flash chromatography
found: 152.0056.
on silica gel (petroleum ether/ethyl acetate 1:1) to give the target
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compound 3w as a white solid (124 mg, 71%). Mp: 315-316 °C; H
1,3-Dihydro-benzoimidazole-2-thione 3q[15]: According to TP, the
residue was purified by flash chromatography on silica gel
(petroleum ether/ethyl acetate 1:1) to give the target compound 3q
as a yellow solid (139 mg, 93%). Mp: 298-300 °C; 1H NMR (400 MHz,
DMSO-d6, TMS): δ (ppm) 12.48 (brs, 2H), 7.10 (s, 4H). 13C NMR (100
NMR (400 MHz, DMSO-d6, TMS): δ (ppm) 13.00 (brs, 2H), 7.57 (d, J
= 8.0 Hz, 2H), 7.29 (d, J = 8.0 Hz, 1H). 13C NMR (100 MHz, DMSO-d6,
TMS): δ (ppm) 171.1, 136.1, 132.8, 127.4, 119.7, 113.3, 110.6,
104.7. HRMS (ESI): Calcd for C8H5N3S (175.0204), found: 175.0217.
MHz, DMSO-d6, TMS): δ (ppm) 168.5, 132.6, 122.7, 109.9. HRMS 5-Trifluoromethyl-1,3-dihydro-benzoimidazole-2-thione
3x[31]
According to TP, the residue was purified by flash chromatography
:
(ESI): Calcd for C7H6N2S (150.0252), found: 150.0263.
on silica gel (petroleum ether/ethyl acetate 1:1) to give the target
5-Chloro-1,3-dihydro-benzoimidazole-2-thione 3r[26]: According to
TP, the residue was purified by flash chromatography on silica gel
(petroleum ether/ethyl acetate 1:1) to give the target compound 3r
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compound 3x as a white solid (111 mg, 51%). Mp: decomposed; H
NMR (400 MHz, DMSO-d6, TMS): δ (ppm) 12.94 (d, J = 12 Hz, 2H),
7.47 (d, J = 8.0 Hz, 1H), 7.38 (s, 1H), 7.32 (d, J = 8.0 Hz, 1H). 13C NMR
(100 MHz, DMSO-d6, TMS): δ (ppm) 170.9, 135.5, 132.7, 127.7 (d,
1C, J = 270 Hz), 123.3 (d, 1C, J = 32 Hz ), 119.9 (d, 1C, J = 4 Hz),
110.1, 106.5 (d, 1C, J = 3 Hz). HRMS (ESI): Calcd for C8H5F3N2S
(218.0126), found: 218.0137.
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as a gray solid (164 mg, 89%). Mp: 298-300 oC; H NMR (400 MHz,
DMSO-d6, TMS): δ (ppm) 12.70 (d, J = 8 Hz, 2H), 7.14 (d, 3H, J = 8.0
Hz). 13C NMR (100 MHz, DMSO-d6, TMS): δ (ppm) 169.7, 133.7,
131.7, 127.1, 122.6, 111.0, 109.6. HRMS (ESI): Calcd for C7H5ClN2S
(183.9862), found: 183.9878.
5-Methyl-1,3-dihydro-benzoimidazole-2-thione 3y[15]: According to
TP, the residue was purified by flash chromatography on silica gel
(petroleum ether/ethyl acetate 1:1) to give the target compound 3y
as a white solid (144 mg, 88%). Mp: 293-294 °C; 1H NMR (400 MHz,
DMSO-d6, TMS): δ (ppm) 12.43 (brs, 2H), 7.03 (d, J = 8.0 Hz, 1H),
6.94 (t, 2H, J = 8.0 Hz), 2.34 (s, 3H). 13C NMR (100 MHz, DMSO-d6,
TMS): δ (ppm) 168.2, 132.95, 132.1, 130.6, 123.6, 110.0, 109.5,
21.4. HRMS (ESI): Calcd for C8H8N2S (164.0408), found: 164.0417.
5-Bromo-1,3-dihydro-benzoimidazole-2-thione 3s[27]: According to
TP, the residue was purified by flash chromatography on silica gel
(petroleum ether/ethyl acetate 1:1) to give the target compound 3s
as a gray solid (194 mg, 85%). Mp: 301-302 °C; 1H NMR (400 MHz,
DMSO-d6, TMS): δ (ppm) 12.70 (d, J = 12 Hz, 2H), 7.27 (d, J = 4.0 Hz,
2H), 7.09 (d, J = 8.0 Hz, 1H). 13C NMR (100 MHz, DMSO-d6, TMS): δ
(ppm) 169.5, 134.1, 132.0, 125.4, 114.8, 112.3, 111.4. HRMS (ESI):
Calcd for C7H5BrN2S (227.9357), found: 227.9369.
6 | J. Name., 2012, 00, 1-3
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