Journal of the Iranian Chemical Society
J=8.5 Hz, Ar-H, C-6), 9.40 (br, 1H, NH); 13C NMR: 26.55
(CH2), 116.5, 117.6, 118.5, 119.5, 121.6, 128.3, 145.0, 162.0
(C=O); Anal. calcd for C9H8ClN3O (209.63): C, 51.56; H,
3.85; N, 20.04; Found: C, 51.64; H, 3.81; N, 19.97.
product remained was triturated with methanol. The solid
product obtained was filtered and crystallized from ethanol.
Acknowledgements The authors would like to extend their sincere
appreciation to Mikko Muuronen, Department of Chemistry, University
of Helsinki, Finland for computed NBO values.
N‑(2‑Amino‑4‑bromo‑phenyl)‑2‑cyanoacetamide
(6b)
References
Yield 87%; IR: ν/cm−1: 3420, 3252 (NH, NH2), 2261 (C≡N),
1664 (C=O); 1H NMR: δ/ppm=3.89 (s, 2H, CH2), 5.31 (br,
2H, NH2), 6.66 (m, 1H, Ar-H), 6.89 (d, 1H, J=1.6 Hz, Ar-H,
C-3), 7.05 (d, 1H, J = 6.8 Hz, Ar-H), 9.39 (br, 1H, NH);
13C NMR: 26.55 (CH2), 116.5, 117.6, 118.5, 119.5, 121.6,
128.3, 145.0, 162.0 (C = O); Anal. calcd for C9H8BrN3O
(254.08): C, 42.54; H, 3.17; N, 16.54; Found: C, 42.67; H,
3.07; N, 16.41.
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N‑(2‑Amino‑4‑methyl‑phenyl)‑2‑cyanoacetamide
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Yield 65%; IR: ν/cm− 1: 3431, 3349, 3219 (NH, NH2),
2263 (C≡N), 1668 (C=O); 1H NMR: δ/ppm=2.14 (s, 3H,
CH3), 3.87 (s, 2H, CH2), 4.87 (br, 2H, NH2), 6.36 (d, 1H,
J = 7.5 Hz, Ar-H), 6.52 (s, 1H, Ar-H, C-3), 6.95 (m, 1H,
Ar-H), 9.36 (br, 1H, NH); 13C NMR: 21.28 (CH3), 26.83
26.6 (CH2), 116.4, 116.7, 117.2, 120.0, 126.4, 136.2, 142.9,
161.7 (C=O); Anal. calcd for C10H11N3O (189.21): C, 63.48;
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Yield 72%; IR: ν/cm−1: 3427, 3334, 3208 (NH, NH2), 2261
(C≡N), 1666 (C=O); 1H NMR: δ/ppm=3.79 (s, 3H, OCH3),
3.88 (s, 2H, CH2), 4.93 (br, 2H, NH2), 6.23 (m, 1H, Ar-H),
6.48 (m, 1H, Ar-H), 6.87 (m, 1H, Ar-H), 9.42 (br, 1H, NH);
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120.3, 126.4, 136.8, 143.2, 162.2 (C=O); Anal. calcd for
C10H11N3O2 (205.21): C, 58.53; H, 5.40; N, 20.48; Found:
C, 58.32; H, 5.38; N, 20.53.
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General procedure for the syntheses
of 2‑(1H‑benzo[d] imidazol‑2‑yl)acetonitrile
N-(Amino-aryl)-2-cyanoacetamide derivatives were fused
above its melting point in an oil-bath for ~15 min. The solid
1 3