Hydrochloric Acid → HCID 86587436, compound

Participants

Reaction Steps

{3-[(tert-Butoxy)carbonylamino]phenyl}-N-(naphthylmethyl) formamide (270 mg, 0.72 mmol) was dissolved in 25 ml of dichloromethane and treated with 7 ml of 2N HCl in ether. After stirring overnight, the precipitate was collected by filtration and dried under vacuum. The aniline (190 mg, 0.61 mmol) was dissolved in dimethylacetamide (10 ml), and 3,5-dichlorobenzoyl chloride (130 mg, 0.61 mmol) and triethylamine (0.5 mL) were added and the resulting mixture was stirred overnight. The product was worked up as described above and recrystallized from ethyl acetate to provide compound 16 as a white crystalline solid, Mp=205-208° C., and 1H NMR (DMSO, 400 MHz) peaks of: δ4.97 (d, 2H, J=5.76); 7.45-8.26 (m, 14H); 9.10 (t, 1H, J=5.76); 10.57 (s, 1H). The theoretical atomic composition for C25H18N2O2Cl2 [C, 66.83; H, 4.04; N, 6.23; Cl; 15.78] compares favorably with that found experimentally [C, 66.73; H, 4.15; N, 6.16; Cl, 15.81].

Provenance & Evidence