Acetone → HCID 178426523, compound

Participants

Reaction Steps

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.

Provenance & Evidence