2,4,5-Trichloronitrobenzene → HCID 19438006, compound

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Reaction Steps

3-Aminocyclopentene hydrochloride (R. Vince and S. Daluge, J. Med. Chem. 1974, 17,578) (5.10 g, 42.8 mmol), 1,2,4-trichloro-5-nitrobenzene (Aldrich, 10.0 g, 42.8 mmol), and potassium carbonate (98%, Aldrich, 15.00 g, 107 mmol) were refluxed in t-butyl alcohol (100 mL) under nitrogen for 24 hours. Volatiles were evaporated in vacuo and the residue chromatographed on silica gel. Title compound was eluted with 20-30% chloroform-hexanes as an orange powder (5.14 g, 44%), m.p. 85°-86° C.; 1H-NMR(DMSO-d6)δ: 8.27 (s, 1, aromatic CH), 7.88 (d, J=7.3 Hz, 1, NH), 7.48 (s, 1, aromatic CH), 6.2-6.0 (m, 1, =CH), 6.0-5.8 (m, 1, =CH), 5.0-4.7 (m, 1, NCH), 2.6-2.2 (m overlapping solvent, 3 CH), 1.8-1.5 (m, 1, 1/2CH2); mass spectrum(CI): 273 (M +1).

Provenance & Evidence