Sodium Hydroxide → N-(1-Pyrazolylmethyl)-N-(4,6-dimethoxypyrimidin-5-yl)-chloroacetamide

Participants

Reaction Steps

347 g of N-(4,6-dimethoxypyrimidin-5-yl)-chloroacetamide, 60 g benzyltriethylammoniumchloride, 3 l CH2Cl2 and 252 g 1-pyrazolylmethylchloride are charged in a sulphonation flask and thereto added, quickly, 750 ml 30% aqueous NaOH (w/w) while cooling on a ice bath. The reaction temperature rises from 13° to 25°. The reaction mixture is further stirred under continued cooling on the ice bath until the temperature reaches 23°. Then the ice bath is removed and the reaction is stirred further for 2 hours. The reaction mixture is then diluted with 1.5 l of water and stirred. The organic phase is partitioned off, dried with Na2SO4 and filtered over a 6 cm SiO2 layer. The SiO2 -layer is washed with 10 l diethylether. The resulting reaction mixture is concentrated to 1.5 l and the precipitate, which has been falling out is filtered off and washed with pentane, then it is dried under vacuum at 50° to give the title compound m.p. 117°-119°.

Provenance & Evidence