Water → HCID 53646179, compound

Participants

Reaction Steps

0.5 g of sodium hydride (80% strength by weight suspension in mineral oil) in 25 ml of anhydrous dimethylformamide was treated dropwise with a solution of 4.4 g of 5-(3-chloro-5-trifluoromethylpyridin-2-yl)benzotriazole in 25 ml of dimethylformamide. After stirring for 15 min, 2.6 g of ethyl bromoacetate were added dropwise, after which the mixture was stirred at 23° C. for 20 hours. The batch was then poured into 200 ml of water. After extracting three times with 100 ml of tert-butyl methyl ether each time, the combined organic phases were washed with 100 ml of water, dried over sodium sulfate and concentrated. The oil residue was purified by means of chromatography on silica gel (eluent: cyclohexane/ethyl acetate=6:1). The following were eluted in succession (without taking into account mixed fractions): 1.0 g of 5-(3-chloro-5-trifluoromethylpyridin-2yl)-2-ethoxycarbonylmethylbenzotriazole; m.p.: 127-129° C.

Provenance & Evidence