Dimethylcarbamoyl Chloride → HCID 23349897, compound

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Reaction Steps

2-(2-Dimethylaminoethylamino)-6-dimethylaminopyrazine (16.5 g., (0.079 mole) is dissolved in 150 ml dry toluene under nitrogen and sodium hydride (50% in mineral oil) (4.17 g., 0.087 mole) is added. The mixture is heated with stirring at 90°-98° C. for 1/2 hour and then refluxed for 1/2 hour. After cooling to 35° C. dimethylcarbamoylchloride (9.35 g., 0.087 mole) is added and the mixture is refluxed for 3 hours and cooled. Ethanol, 5 ml is added and the solvents are removed under reduced pressure. The residue is dissolved in dilute hydrochloric acid and extracted with ether. The aqueous layer is made alkaline with aqueous sodium hydroxide with a cooling bath to maintain the temperature below 35° C. The alkaline solution is extracted with methylene chloride. The organic extracts are washed with saturated sodium chloride solution, dried over sodium sulfate and concentrated under vacuum. The residual oil is dissolved in isopropanol, 50 ml and diethyl ether, 300 ml and then gaseous hydrogen chloride is passed into the solution. The product dihydrochloride crystallizes, is filtered, and washed with 100 ml of 1:1 acetone: isopropanol. Recrystallization from 150 ml isopropanol and 75 ml of diethyl ether yields 8 g. (0.029 mole) of the dihydrochloride salt, melting point 189° C. (dec).

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