Methane → 6-(3,4-Dichlorophenoxy)-3-(ethylthio)-2-pyridinecarbonitrile

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Reaction Steps

In a reaction flask were placed 110 ml of THF, 10 ml of DMSO and 5.6 g of t-BuOK. 3,4-Dichlorophenol (8.2 g) was added and the mixture was stirred until solution was achieved. To this was added 9.9 g of 6-chloro-3-ethylthio-2-pyridinecarbonitrile and the reaction mixture was heated at reflux temperature for about 5 hours. After cooling, the contents of the flask were poured onto 500 g of ice, stirred until the ice had melted and then filtered. The solid obtained by filtration was dissolved in CH2Cl2, treated with charcoal, dried and was concentrated. Upon dilution with hexane, 12.6 g (77.5%) of 6-(3,4-dichlorophenoxy)-3-ethylthio-2-pyridinecarbonitrile was obtained as a tan crystalline material, m.p. 64°-66° C. Subsequent analysis by differential scanning calorimetry indicated that the compound obtained was polymorphic and existed in two crystalline forms: one melting at 66°-69° C., and the other at 81°-87° C.

Provenance & Evidence