3,5-Dichlorophenyl isothiocyanate → HCID 10230282, compound

Participants

Reaction Steps

A solution of 2-bromo-5-(2-naphthylmethoxy)phenylamine (100 mg, 0.3 mmol) and 3,5-dichlorophenylisothiocyanate (60 mg, 0.3 mmol) in 10 mL of dichloromethane was stirred at room temperature for 16 h. The reaction mixture was evaporated to dryness and the residue recrystallized from ethyl acetate/hexane to give 60 mg of product in (38%) yield as a white solid: mp 149-151° C. 1H NMR (400 MHz, Me2SO-d6) δ5.56 (s, 2H); 7.02 (dd, 1H, J=3.0, 8.9); 7.29 (d, 1H, J=3.0); 7.35 (t, 1H, J=1.8); 7.49-7.69 (m, 7H); 7.93-7.99 (m, 2H); 8.07-8.10 (m, 1H); 9.78 (s, 1H); 10.10 (s, 1H). Anal. Calcd for C24H17BrCl2N2OS: C, 54.16; H, 3.22; N, 5.26; S, 6.02; Cl, 13.32; Br, 15.01. Found: C, 54.17; H, 3.32; N, 5.28; S,6.10; Cl, 13.31; Br, 15.00.

Provenance & Evidence