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RSC Advances
Journal Name
Tert-butyl phenylcarbamate
ARTICLE
.
1H-NMR (250 MHz, 298K, CDCl3)
DOI: 10.1039/C6RA17268G
Reaction afforded white crystals (89% yield), mp = 134-135 °C 1.63 (sex, J = 7.5 Hz, 2H), 2.50 (s, 3H), 4.08 (t, J = 7.5 Hz, 2H),
(lit.41 133-137 °C). 1H-NMR (250 MHz, 298K, CDCl3),
1.45 (s, 9H), 6.42 (s, br, 1H, NH), 6.95 (m, 1H), 7.26 (m, 4H). 13C- 2H) . 13C-NMR (63 MHz, 298K, CDCl3),
ppm; 6.95 (s,br, 1H, NH), 7.43 (d, J = 7.5 Hz, 2H), 7.85 (d, J = 7.5 Hz,
ppm; 10.31, 22.18,
ppm; 28.33, 68.98, 118.50, 26.38, 67.22, 117.54, 129.87, 130.88, 142.51, 153.21, 200.49.
NMR (63 MHz, 298K, CDCl3),
123.00, 128.96, 134.38, 156.00.
Propyl (naphthalen-1-yl)carbamate.
Cyclohexyl phenylcarbamate.
Reaction afforded white crystals (90% yield), mp = 73-75 °C.
Reaction afforded white crystals (90 % yield), mp = 79-80 °C 1H-NMR (250 MHz, 298K, CDCl3)
ppm; 0.90 (t, J = 7.5 Hz, 3H),
1
(lit.39 80-81 °C). H-NMR (250 MHz, 298K, CDCl3),
ppm; 0.86 1.63 (sex, J = 7.5 Hz, 2H), 4.09 (t, J = 7.5 Hz, 2H), 6.90 (s, br, 1H,
(m, 4H), 1.19 (m, 4H), 1.41-1.66 (m, 2H), 4.77 (qunt, J = 5.5 Hz, NH), 7.34-7.81 (m, 7H). 13C-NMR (63 MHz, 298K, CDCl3),
1H), 6.62 (s, br, 1H, NH), 6.96 (m, 1H), 7.24 (m, 4H). 13C-NMR ppm; 10.37, 22.31, 67.11, 120.50, 124.92, 125.80, 125.95,
(63 MHz, 298K, CDCl3), ppm; 9.70, 19.71, 29.01, 73.25, 126.16, 128.70, 128.79, 130.88, 132.60, 134.06, 154.64.
118.57, 123.17, 129.00, 138.16, 153.49.
Propyl (benzo[d][1,3]dioxol-5-yl)carbamate
Reaction afforded white crystals (88% yield), mp = 78-80 °C.
Reaction afforded white crystals (84% yield), mp = 105-107 °C. 1H-NMR (250 MHz, 298K, CDCl3)
ppm; 0.96 (t, J = 7.5 Hz, 3H),
[α]17-D -120 C (0.05, CDCl3). H-NMR (250 MHz, 298K, CDCl3) 1.67 (sex, J = 7.5 Hz, 2H), 4.10 (t, J = 7.5 Hz, 2H), 5.92 (s, 2H),
ppm; 0.72-1.00 (m, 12H), 1.33 (m, 2H), 1.62 (m, 2H), 1.99 (m, 6.70 (m, 3H), 7.08 (s,br, 1H, NH) .13C-NMR (63 MHz, 298K,
2H), 4.59 (m, 1H), 6.55 (s, br, 1H, NH), 6.96 (m, 1H), 7.28 (m, CDCl3), ppm; 10.34, 22.29, 66.83, 101.18, 108.05, 111.98,
4H). 13C-NMR (63 MHz, 298K, CDCl3),
ppm; 16.42, 20.81, 114.89, 128.81, 143.67, 147.89, 154.11.
.
(-)Menthyl phenylcarbamate
.
o
1
22.04, 23.46, 26.24, 31.39, 34.24, 41.34, 47.32, 75.08, 118.43,
123.14, 129.01, 138.16, 153.13.
Propyl (thiophen-3-yl)carbamate.
Reaction afforded white crystals (85% yield), mp = 70-72 °C.
Benzyl phenylcarbamate.
1H-NMR (250 MHz, 298K, CDCl3)
ppm; 0.89 (t, J = 7.5 Hz, 3H),
The reaction afforded white crystals (90% yield), mp = 70-72 °C 1.62 (sex, J = 7.5 Hz, 2H), 4.06 (t, J = 7.5 Hz, 2H), 6.53 (s, br, 1H,
1
(lit.42 71-73 °C). H-NMR (250 MHz, 298K, CDCl3),
(s, 2H), 6.84 (s, br, 1H, NH), 7.02 (m, 1H), 7.09-7.38 (m, 9H). (63 MHz, 298K, CDCl3),
13C-NMR (63 MHz, 298K, CDCl3),
ppm; 66.91, 118.77, 123.43, 120.70, 124.73, 153.26.
126.94, 128.24, 128.55, 128.97, 136.05, 137.82, 153.43.
ppm; 5.16 NH), 6.87 (d, J = 5.5 Hz, 2H), 7.14 (d, J = 5.5 Hz, 1H). 13C-NMR
ppm; 10.31, 22.25, 66.98, 107.78,
Propyl (4-boromophenyl)carbamate
Reaction afforded white crystals (91% yield), mp = 76-78 °C
Reaction afforded white crystals (91% yield), mp = 52-54 °C (lit.45 77-78 °C). 1H-NMR (250 MHz, 298K, CDCl3)
ppm; 0.96 (t,
(lit.43 53-54 °C). 1H-NMR (250 MHz, 298K, CDCl3)
ppm; 0.88 (t, J = 7.5 Hz, 3H), 1.69 (sex, J = 7.5 Hz, 2H), 4.12 (t, J = 7.5 Hz, 2H),
J = 7.5 Hz, 3H), 1.61 (sex, J = 7.5 Hz, 2H), 2.21 (s, 3H), 4.03 (t, J = 6.76 (s, br, 1H, NH), 7.28 (d, J = 7.5 Hz, 2H), 7.39 (d, J = 7.5 Hz,
7.5 Hz, 2H), 6.62 (s,br, 1H, NH), 7.02 (d, J = 7.5 Hz, 2H), 7.18 (d, 2H). 13C-NMR (63 MHz, 298K, CDCl3),
ppm; 10.34, 22.23,
J = 7.5 Hz, 2H) . 13C-NMR (63 MHz, 298K, CDCl3),
ppm; 10.36, 67.03, 120.19, 128.41, 131.92, 132.10, 153.59.
.
Propyl (4-methylphenyl)carbamate
.
20.73, 22.30, 66.74, 118.83, 126.69, 129.49, 135.44, 153.94.
Propyl (4-chlorophenyl)carbamate.
Reaction afforded white crystals (93% yield), mp = 82-84 °C.
ppm; 0.90 (t, J = 7.5 Hz, 3H),
ppm; 0.98 (t, J = 7.5 Hz, 3H), 1.62 (sex, J = 7.5 Hz, 2H), 4.05 (t, J = 7.5 Hz, 2H), 6.63 (s, br, 1H,
1.71 (sex, J = 7.5 Hz, 2H), 4.15 (t, J = 7.5 Hz, 2H), 6.83 (s, br, 1H, NH), 7.18 (d, J = 9 Hz, 2H), 7.26 (d, J = 9 Hz, 2H). 13C-NMR (63
NH), 7.50 (d, J = 10 Hz, 2H), 7.59 (d, J = 10 Hz, 2H). 13C-NMR (63 MHz, 298K, CDCl3),
ppm; 10.32, 22.22, 67.03, 119.82, 128.28,
MHz, 298K, CDCl3), ppm; 10.28, 22.13, 67.44, 106.17, 115.52, 129.00, 136.58, 153.60.
Propyl (4-cyanophenyl)carbamate.
Reaction afforded white crystals (95% yield), mp = 88-90 °C. 1H-NMR (250 MHz, 298K, CDCl3)
1H-NMR (250 MHz, 298K, CDCl3)
118.18, 133.36, 146.33, 158.66.
Conclusion
Propyl (4-nitrophenyl)carbamate.
Reaction afforded white crystals (96% yield), mp = 114-115 °C
(lit.44 115 °C). 1H-NMR (250 MHz, 298K, CDCl3)
ppm; 0.90 (t, J
In conclusion, we report here a new heterogeneous method for the
arylation of various carbamates with aryl halides. The procedure is
interesting due to some advantageous such as high yields, using a
heterogeneous catalyst, easy separation and recyclability of catalyst
and relatively short reaction times. The catalyst can be easily
removed from the reaction mixture by an external magnetic field
and reused for at least 6 runs.
= 7.5 Hz, 3H), 1.64 (sex, J = 7.5 Hz, 2H), 4.09 (t, J = 7.5 Hz, 2H),
7.07 (s, br, 1H, NH), 7.50 (d, J = 7.5 Hz, 2H), 8.12 (d, J = 7.5 Hz,
ppm; 10.26, 22.12,
67.55, 117.66, 125.19, 130.94, 144.13, 153.02.
2H). 13C-NMR (63 MHz, 298K, CDCl3),
Propyl (4-acetylphenyl)carbamate.
Reaction afforded white crystals (90% yield), mp = 112-114 °C.
This journal is © The Royal Society of Chemistry 20xx
J. Name., 2013, 00, 1-3 | 7
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