M-Phenylenediamine → HCID 43602671, compound

Participants

Reaction Steps

Into a 1-neck round-bottom flask were added m-phenylenediamine (1.6 g, 14 mmol) and tetrahydrofuran (30 mL) and triethylamine (2.0 mL, 14 mmol). The mixture was cooled in ice bath and then m-nitrobenzenesulfonyl chloride (2.1 g, 9.6 mmol) was slowly added. The resultant mixture was warmed up to rt. after 1 h and EtOAc and water were then added. Aqueous layer was extracted again with EtOAc. The organics layers were combined, dried over Na2SO4 and the solvent was removed under vacuum. The crude was purified by silica gel column chromatography to give the desired product (2.5 g, 89%). LCMS for C12H11N3O4S (M+H)+: m/z=294.0. 1H NMR (300 MHz, CD3OD): δ 8.56 (t, J=2.0 Hz, 1H), 8.40 (ddd, J=8.2, 2.3, 1.2 Hz, 1H), 8.09 (ddd, J=7.8, 1.7, 1.0 HZ, 1H), 7.73 (t, J=8.1 Hz, 1H), 6.91 (t, J=8.1 Hz, 1H), 6.51 (t, J=2.2 Hz, 1H), 6.42 (ddd, J=8.1, 2.2, 1.0 Hz, 1H), 6.36 (ddd, J=7.9, 2.1, 1.0 Hz, 1H).

Provenance & Evidence