P-Anisidine → N-(4-methoxyphenyl)-2-nitrobenzenesulfonamide

Participants

Reaction Steps

A 250 mL round bottom flask was equipped with a magnetic stirrer, charged with p-anisidine (13.0 mmol), followed by dichloromethane (75 mL). The flask was then placed in an ice bath to chill the contents. Triethylamine was added and an addition funnel was installed. The addition funnel was charged with 2-nitrobenzenesulfonyl chloride (32.4 mmol) in dichloromethane (75 mL). The sulfonyl chloride was added dropwise very slowly and the reaction monitored by TLC (dichloromethane/silica) several times during the addition. The reaction was complete after addition of 50 mL (21.6 mmol) of the sulfonyl chloride solution. The reaction solvent was removed at 0° C. and immediately loaded onto a 600 mL sintered glass funnel charged with silica gel (400 g), eluted with dichloromethane collecting 100 mL fractions. Fractions containing the desired product were combined and evaporated under diminished pressure to yield the title compound as a yellow powder in excellent yield. 3.67 g, (92%). 1H-NMR (CDCl3): δ 3.20 (s, 3H); 6.78-6.79 (d, 2H, J=8.9 Hz); 7.07-7.10 (d, 3H, J=8.9 Hz); 7.53-7.58 (t, 1H, J=7.7 Hz); 7.66-7.71 (t, 1H, J=7.8 Hz); 7.73-7.76 (d, 1H, J=7.8 Hz); 7.84-7.87 (d, 1H, J=7.9 Hz).

Provenance & Evidence