Reacción #2358567

Ecuación de reacción

water

3,4-dimethoxybenzenesulfonyl chloride

N-hexyl-3,4-dimethoxybenzenesulfonamide

NaH

→

N-(3,4-dimethoxyphenylsulfonyl)-N-hexyl-3,4-dimethoxybenzenesulfonamide

Rendimiento 25.0%

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.WAITAfter a further 1 hr
2. 2
   Otroforming a white solid
3. 3
   FiltraciónThe solid was filtered
4. 4
   Otrorecrystallized from methanol

Procedimiento

To a stiffing solution of N-hexyl-3,4-dimethoxybenzenesulfonamide (0.250 g, 0.830 mmol) in 3.30 mL of DMF, NaH (0.037 g, 0.913 mmol; 60% in oil dispersion) was added. After 30 mins, 3,4-dimethoxybenzenesulfonyl chloride (0.222 g, 0.937 mmol) was added. After a further 1 hr, the reaction solution was poured over water (15 mL) forming a white solid. The solid was filtered and recrystallized from methanol to afford 0.103 g (25%) of N-(3,4-dimethoxyphenylsulfonyl)-N-hexyl-3,4-dimethoxybenzenesulfonamide as a white solid. 1H NMR (acetone-d6, 400 MHz) δ 7.62 (dd, J=2.9, 8.2 Hz, 2H), 7.57 (d, J=2.3 Hz, 2H), 6.94 (d, J=8.6 Hz, 2H), 3.95 (s, 12H), 3.60 (m, 2H), 1.63 (m, 2H), 1.21 (m, 6H), 0.85 (t, J=6.8 Hz, 3H); 13C NMR (acetone-d6, 100 MHz) δ 150.05, 144.99, 131.10, 121.34, 115.05, 115.00, 49.00, 31.65, 26.38, 22.45, 13.51.

Fuente