Aniline → HCID 19106876, compound

Participants

Reaction Conditions

Reaction Steps

A stirred suspension of (±)-N-methyl-2-oxo-1-(3-pyridyl)cyclohexanecarbothioamide (2.5 g) and aniline (3.72 g) in anhydrous dichloroethane (30 ml) under an argon atmosphere was treated dropwise at 25° C. with titanium tetrachloride (0.8 ml). The reaction mixture was stirred at 25° C. until completion of the reaction (as judged by TLC analysis), and then it was poured into a solution of sodium bicarbonate (16.8 g) in water (100 ml) and stirred for 15 minutes. The mixture was filtered through a pad of celite and the aqueous layer was extracted with dichloromethane (3×75 ml). The combined organic solution was washed with aqueous sodium bicarbonate solution (100 ml; 10% w/w), with water (50 ml) and with saturated brine (100 ml), and then it was dried over sodium sulphate and concentrated in vacuo, to give N-methyl-2-phenylimino-1-(3-pyridyl)cyclohexanecarbothioamide in the form of a crude oil.

Provenance & Evidence