Triethylamine → 1-(4-Chloro-3-trifluoromethyl-phenyl)-3-(3-nitro-benzyl)-urea

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Reaction Steps

To a round bottom flask was added 4-chloro-3-(trifluoromethyl)-phenyl isocyanate (443 mg, 2.0 mmol, 1.0 eq.) and acetonitrile (3.0 mL). The solution was cooled to 0° C. before a mixture of 3-nitrobenzylamine HCl (377 mg, 2.0 mmol, 1.0 eq.), DMP (1.0 mL), and triethyl amine (0.27 mL, 2.0 mmol, 1.0 eq.) was added dropwise. The reaction was then allowed to warm to RT slowly, and then stirred for an additional 2 h. The reaction was then concentrated to remove acetonitrile. EtOAc and water were added, and the mixture was extracted, washed with brine, dried with Na2SO4, and concentrated to give an oil. Upon sitting at RT, the oil crystallized to give urea 26 (728 mg, 97% yield). LC/MSD (HP Series 1100 MSD) MS (ES+) m/z 374.1 (M+H)+1 1H-NMR, Varian 400 MHz (DMSO-d6) δ 9.23 (br. s, 1H), 8.14 (m, 1H), 8.09 (m, 1H), 8.04 (d, 1H), 7.74 (d, 1H), 7.62 (m, 2H), 7.52 (d, 1H), 7.04 (br t, 1H), 4.40 (s, 2H) ppm.

Provenance & Evidence