Ethanol → HCID 21329557, compound

Participants

Reaction Steps

A mixture of 6.66 g. (0.041 mole) of N2 -methyl-5-isopropyl-1,2-phenylenediamine and 10.02 g. (0.081 mole) of ethyl methylcarboximidate hydrochloride in 100 ml. of absolute ethanol was stirred at room temperature for 40 hours and then refluxed for 18 hours. The reaction mixture was distilled to dryness under reduced pressure, 100 ml. of 4N HCl was added to the residue and then the mixture refluxed for 22 hours. After cooling, the resultant mixture was filtered and the filtrate added dropwise to 200 ml. of stirred ice and water containing 50 ml. of conc. ammonium hydroxide. The precipitated product was isolated by filtration, washed with water and then air-dried. The crude product was dissolved in 75 ml. of refluxing cyclohexane, filtered and the filtrate allowed to cool. The desired product crystallized from the cooled cyclohexane and was removed by filtration to give 2.73 g. (35.8%), melting at 130°-131° C.

Provenance & Evidence