Hydrochloric Acid → 1-Methyl-1-(1,2,3,4-tetrahydro-1-naphthyl)urea

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Reaction Steps

To a stirred solution of 8.05 grams (0.05 mole) of 1,2,3,4-tetrahydro-N-methyl-1-naphthylamine in 10 ml. of methanol is added a solution of 4.2 ml. of 12N hydrochloric acid (0.05 mole) in 35 ml. of water. The mixture is cooled in an ice-water bath while a solution of 4.46 grams (0.055 mole) of potassium cyanate in 15 ml. is added dropwise. After the addition is complete, the reaction mixture is stirred at room temperature for 45 minutes and then at 70° to 75° C. for 30 minutes. The mixture is cooled to 25° C., and the solid product filtered off, washed with water and then with cold ethyl acetate. The dried product weighs 7.1 grams and has melting point 160°-163° C. Recrystallization from acetone-hexane gives the analytical sample, melting point 161° to 163° C. Recrystallization from acetone-hexane gives the analytical sample, melting point 161° to 163° C. Analysis Calculated for C12H16N2O: C, 70.56; H, 7.90; N, 13.72. Found: C, 70.60; H, 7.94; N, 13.75.

Provenance & Evidence