Methyl iodide → 4-bromo-N-methyl-N-(tetrahydro-furan-2-ylmethyl)-benzenesulfonamide

Participants

Reaction Steps

4.30 g of 4-bromo-N-(tetrahydro-furan-2-ylmethyl)-benzenesulfonamide (compound D2) are dissolved in 150 ml of dry tetrahydrofuran. 590 mg of sodium hydride (strength 60 wt. % dispersion in mineral oil) are added in portions to the solution. After 15 min, 1.67 ml of methyl iodide are slowly added and the reaction mixture is stirred at room temperature for 20 hours. Subsequently, the suspension is concentrated in vacuo, extracted using 200 ml of ethyl acetate and 100 ml of half-saturated brine (sodium chloride solution). The organic layer is dried using Na2SO4, filtered with suction, and concentrated in vacuo to yield 4.53 g of the title compound as an oil. ESI-MS: 334.2/336.0 (MH+, 100%:98%). TLC: Rf=0.78 (dichloromethane/ethanol 20:1 parts by volume).

Provenance & Evidence