Ammonium Chloride → HCID 58956317, compound

Participants

Reaction Steps

4-(Prop-2-ynylaminosulfonylmethyl)nitrobenzene (0.437 g, 1.72 mmol), iron (0.48 g, 8.6 mmol), and NH4Cl (0.24 g, 4.5 mmol) were vigorously stirred in ethanol:water (1:1, 40 mL) at 70° C. for 25 minutes. The reaction mixture was filtered hot through Celite and concentrated in vacuo. The residue was suspended in 10% 2N ammoniacal methanol in dichloromethane, sonicated, and filtered through Celite. Concentration gave 4-(Prop-2-ynylaminosulfonylmethyl)aniline as a brown oil which was purified by column chromatography (silica gel, dichloromethane ramped to methanol:dichloromethane (0.75:100)). 1H NMR (DMSO-d6): δ 7.45 (t, J=5.4 Hz, 1H), 6.99 (d, J=8.1 Hz, 2H), 6.50 (d, J=8.1 Hz, 2H), 5.15 (s, 2H), 4.12 (s, 2H), 3.68 (dd, J=2.1 and 5.7 Hz, 2H), 3.31 (t, J=2.1 Hz, 1H); LCMS: purity: 97%; MS (m/e): 225 (MH+).

Provenance & Evidence