Triethylamine → HCID 54188717, compound

Participants

Reaction Steps

To a solution of [S-(R*,R*)] and [R-(R*,R*)]-N-(2-amino-1,2-diphenylethyl)-N'-(4-chlorophenyl)urea (0.1 g, 0.27 mmol) in dichloromethane (5 mL) is added triethyl amine (0.03 g, 0.27 mmol) followed by indole-3-acetic acid chloride (0.05 g, 0.27 mmol). The mixture is stirred 1.5 hours at room temperature before diluting with diethyl ether and washing with aqueous 2M HCl, aqueous 1M NaOH, saturated aqueous NaCl, and drying (MgSO4). Filtration and concentration gives an oil which is purified by flash chromatography (SiO2, EtOAc/hexane eluent) to provide 0.05 g (33%) of desired product, mp 224°-227° C. IR (KBr): 3360, 1549, 1492, 1226, 698 cm-1 ; NMR (DMSO-d6): 3.56 (s, 2H), 5.07 (m, 2H), 6.78-7.45 (m, 20H), 8.65 (m, 2H), 10.81 (s, 1H). Analysis calculated for C31H27ClN4O2.0.5H2O: C, 69.98; H, 5.30; N, 10.53. Found: C, 69.65; H, 5.41; N, 10.56.

Provenance & Evidence