Sodium hydride → HCID 13674813, compound

Participants

Reaction Conditions

Reaction Steps

1.0 g of a 80% mineral oil dispersion of sodium hydride is added in small portions, at room temperature, to a mixture of 6.0 g (30 mmoles) of N-(2,6-dimethylphenyl)-methanesulfonamide and 100 ml of dry toluene, and the resulting mixture is heated to 100° C. within 0.5 hours. 7.0 g (30 mmoles) of 1,2-bis(methanesulfonyloxy)-propane are added to the mixture at 100°-105° C. within one hour, and the reaction mixture is stirred at the same temperature for 5 hours. The mixture is cooled, washed thrice with 20 ml of water, twice with 25 ml of 1 n aqueous sodium hydroxide solution and then thrice with 30 ml of water, each, dried over anhydrous magnesium sulfate, and the solvent is evaporated under reduced pressure. The resulting oily substance, weighing 5.9 g, is triturated with diethyl ether to obtain 4.4 g (44%) of a crude, solid product, m.p.: 70°-80° C. The crude product is recrystallized twice from isopropanol to obtain 1.85 g (18.5%) of 1-[N-(2,6-dimethylphenyl)-methanesulfonamido]-2-methanesulfonyloxy-propane, m.p.: 117°-120° C. This compound is identical with the product obtained according to Method (A).

Provenance & Evidence