Dimethylformamide → HCID 13069836, compound

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Reaction Steps

To a mixture of 186 g. (1 mole) of 2,4-dichlorobenzyl cyanide and 60 g. (1.1 mole) of powdered potassium hydroxide in 400 ml. of dry dimethyl formamide is added 75 g. (1 mole) of 1,2-epoxy butane dropwise at 10° C. The resulting brown reaction mixture is stirred at room temperature overnight. It is then poured into water and extracted with ether. The combined ether extracts are washed with water, 5% sodium chloride solution and dried over magnesium sulfate. Solvent is evaporated to give 228 g. of a brown oil which is assigned the iminolactone structure due to strong ir absorption at 1680 cm-1. This material is redissolved in toluene and 300 ml. 25% hydrochloric acid are added. The mixture is heated over a steam bath for two hours. The organic layer is separated and washed with water, saturated sodium chloride solution and dried over magnesium sulfate. Solvent is evaporated to give a light yellow oil which is further purified by vacuum distillation (150° C./0.2 mm) to give 200 g. of desired product.

Provenance & Evidence