Ethyl chloroacetate → HCID 14099036, compound

Participants

Reaction Steps

0.12 g of sodium hydride (as a 55% w/w dispersion in mineral oil) was added to a solution of 0.55 g of 4,5-dihydro-5-methyl-6-(p-hydroxyphenyl)-1,2,4-triazin-3(2H)-one [prepared as described in step (a) above] dissolved in 6 ml of dimethylformamide, whilst ice-cooling and stirring, and the mixture was stirred at room temperature for 30 minutes. At the end of this time, 0.33 g of ethyl chloroacetate was added. The mixture was then heated at 105° to 110° C. for 3 hours, whilst stirring. The dimethylformamide was then distilled off under reduced pressure, and the residue was diluted with water, after which the mixture was extracted with methylene chloride. The extract was dried over anhydrous magnesium sulfate, and then subjected to column chromatography through silica gel eluted with a 1:50 by volume mixture of ethanol and methylene chloride to give a brown oil. This oil was triturated with ethyl acetate to give crystals, which were recrystallized from ethyl acetate, to give 0.43 g of the title compound as pale yellow needles melting at 152°-153° C.

Provenance & Evidence