Thiourea, N-[[3-(trifluoromethyl)phenyl]methyl]- synthesis

Yield:296277-06-0 12%

Reaction Conditions:

Stage #1: 3-(TRIFLUOROMETHYL)BENZYLAMINEwith hydrogenchloride in water;Cooling with ice;
Stage #2: potassium thioacyanate in tetrahydrofuran;water at 80; for 24 h;

Steps:

General procedure of the synthesis of benzylthiourea derivatives (2a-2g)

General procedure: Benzylamine was added to the reaction flask in ice bath. Thenc-HCl was slowly added to afford a salt. This salt was dissolved in THF then KSCN (1.5 equiv) was added. The reaction mixture was stirred at 80 °C for 24 h.The reaction progress was monitored by TLC and the solvent was removed invacuoand then added H₂O, extracted with EtOAc, the organic layer was dried over MgSO₄, filtered, concentrated invacuo. The residue was purified by silica gel column chromatography (17% EtOAc/hexanes) to afford desired product.

References:

Jo, Hyeju;Zhou, Yuanyuan;Viji, Mayavan;Choi, Minho;Lim, Jae Young;Sim, Jaeuk;Rhee, Jeongtae;Kim, Youngsoo;Seo, Seung-Yong;Kim, Wun-Jae;Hong, Jin Tae;Lee, Heesoon;Lee, Kiho;Jung, Jae-Kyung [Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,# 21,p. 4854 - 4857] Location in patent:supporting information