2-Nitrobenzenesulfonyl Chloride

Used Chemicals

• 2-Nitrobenzenesulfonyl Chloride (= o-Ns-Cl) [N0142]
• 4-Methoxybenzylamine [M0870]
• Triethylamine (= Et₃N) [T0424]
• Dichloromethane

Procedure

To a solution of 4-methoxybenzylamine (1.00 g, 7.29 mmol) and triethylamine (1.11 mL, 8.02 mmol, 1.1 eq.) in dichloromethane (14.6 mL) was added o-Ns-Cl (1.70 g, 7.65 mmol, 1.05 eq.) at 0 °C and the mixture was stirred for 2 h at room temperature. The reaction mixture was quenched with 1 mol/L HCl aq. (14.6 mL) with cooling to 0 °C and the water layer was extracted with dichloromethane (4 x 10 mL). The combined organic layer was washed with brine, dried over sodium sulfate and filtered to give 1 as a pale yellow solid (2.32 g, 99% yield).

Experimenter’s Comments

The reaction mixture was monitored by TLC (ethyl acetate:hexane = 1:1, Rf = 0.6).

Analytical Data

Compound 1

¹H NMR (270 MHz, DMSO-d₆); δ 8.57 (t, J = 6.2 Hz, 1H), 7.75-7.92 (m, 4H), 7.15 (d, J = 8.8 Hz, 1H), 6.79 (d, J = 8.8 Hz, 1H), 4.08 (d, J = 6.2 Hz, 1H), 3.70 (s, 3H).

Other Reference

• PREPARATION OF SECONDARY AMINES FROM PRIMARY AMINES VIA 2-NITROBENZENESULFONAMIDES: N-(4-METHOXYBENZYL)-3-PHENYLPROPYLAMINE
• W. Kurosawa, T. Kan, T. Fukuyama, Org. Synth. 2002, 79, 186.

References

• W. Kurosawa, T. Kan, T. Fukuyama, Org. Synth. 2002, 79, 186.