Tetrafluoro-m-phenylenediamine dihydrochloride → HCID 20637335, compound

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2,5-Bis[2-chloro-4-(2-pyridylimino)aminophenyl]furan (4j, DB712) was prepared according to the procedure for 4f using diamine 3d and S-(2-naphthylmethyl)2-pyridylthioimidate hydrobromide as starting materials. Free base: orange crystalline solid, mp 189-190° C. (EtOH). Yield: 25%. 1H NMR (DMSO-d6): 6.85 (br s, 4NH), 7.02 (dd, 2H), 7.08 (d, 2H), 7.17 (s, 2H), 7.56 (m, 2H), 7.93-7.98 (m, 4H), 8.29 (d, 2H), 8.64 (m, 2H). Dihydrochloride: yellow/orange solid, mp>180° C. dec. 1H NMR (DMSO-d6): 7.45 (s, 2H), 7.60 (d, 2H), 7.80 (s, 2H), 7.86 (dd, 2H), 8.23 (m, 4H), 8.50 (d, 2H), 8.90 (d, 2H), 9.54 (br s, 2H), 10.23 (br s, 2H), 11.98 (br s, 2H). MS (EI): m/z 530, 528, 526 (M+, 13.2, 69.8, 100), 426, 424, 422 (7.9, 48, 72.4), 322, 320, 318 (2.6, 17.4, 26.6). Anal. Calcd. for C28H20Cl2N6O.2.0HCl.1.5H2O (627.35): C, H, N, Cl.

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