反应详情

4-Tolylthiourea (33.2 g., 0.2 mole) in 200 ml. acetone is heated under reflux for 3 hrs. with methyliodide (31.4 g., 0.221 mole). Solvent is removed in vacuo and the resulting 2-methyl-1-(4-tolyl)-2-thiopseudourea hydroiodide dissolved in 200 ml. tert-butanol. Pyrrolidine (28.4 g., 0.4 mole) is added and the mixture heated at reflux for 18 hrs. The reaction mixture is cooled, diluted with ether and the resulting solid separated. Recrystallization from acetone-ether affords N-(4-tolyl)-1-pyrrolidinecarboximidamide hydroiodide, m.p. 166°-168° C. Conventional treatment of the salt in CH2Cl2 with aqueous (10-20%) NaOH affords the corresponding free base.

1. temperatureunder reflux for 3 hrs
2. customSolvent is removed in vacuo
3. dissolutionthe resulting 2-methyl-1-(4-tolyl)-2-thiopseudourea hydroiodide dissolved in 200 ml
4. temperaturethe mixture heated
5. temperatureat reflux for 18 hrs
6. temperatureThe reaction mixture is cooled
7. customthe resulting solid separated
8. customRecrystallization from acetone-ether