N-(2-Chloro-5-cyanophenyl)-4,4,4-trifluorobutanamide (3) was synthesized by reacting 4,4,4-trifluorobutanoic acid (1) with 2-amino-4-chlorobenzonitrile (2) in the presence of triethylamine and propylphosphonic anhydride in ethyl acetate. Characterization of the compound was done by IR, 1H-NMR, 13C-NMR, LC-MS and CHN analysis.
Molbank 2013, 2013(3), M803; doi:10.3390/M803
Short Note
N-(2-Chloro-5-cyanophenyl)-4,4,4-trifluorobutanamide
 | Dr. S. Sreenivasa , Associate Professor, Tumkur University |
email...........drsreenivasa@yahoo.co.in.
1 Center for Advanced Materials, Department of Chemistry, Tumkur University, Tumkur-572103, India2 Tadimety Aromatics Pvt. Ltd, Hirehalli Industrial Area, Tumkur-572168, India
* Author to whom correspondence should be addressed.
Synthesis of N-(2-Chloro-5-cyanophenyl)-4,4,4-trifluorobutanamide (3)
compound (3) as a colorless solid with Rf = 0.79.
Yield: 1.63 g (90%).
Melting point: 151–153 °C.
MS: m/z = 277.64 (M++1).
IR: νmax/cm−1: 3340 (N-H), 2228 (CN), 1698 (CO), 1342–1140 (CF3 streching).
1H-NMR (DMSO-d6) δ: 10.47 (s, 1H, NH), 7.88 (d, J = 8.7 Hz, 1H, Ar-H), 7.80 (d, J = 1.9 Hz, 1H,
Ar-H), 7.45 (dd, J = 8.3 Hz and J = 1.5 Hz, 1H, Ar-H), 2.74 (t, J = 7.5 Hz, 2H, COCH2),
2.67–2.55 (m, 2H, CF3CH2).
13C-NMR (DMSO-d6) δ: 169.3, 141.2, 138.3, 134.8, 128.7 CF3, 125.9, 124.6, 115.9, 104.9, 28.7, 27.8.
Elemental analysis: Calculated for C11H8ClF3N2O: C, 47.76%; H, 2.91%; N, 10.13%. Found: C,
47.79%; H, 2.96%; N, 10.19%.
Center for Advanced Materials, Department of Chemistry, Tumkur University, Tumkur-572103, India
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