5-[(2-chlorophenoxy)methyl]-1,3,4-Thiadiazol-2-amine synthesis

Yield:84138-74-9 60%

Reaction Conditions:

Stage #1: 2-{[(2-chlorophenyl)oxy]acetyl}hydrazinecarbothioamidewith methanesulfonic acid in toluene; for 2 h;Heating / reflux;
Stage #2: with ammonia in water; pH=9;

Steps:

9

To a solution of 2-{[(2-chlorophenyl)oxy]acetyl}hydrazinecarbothioamide (Intermediate 8) (36.6 g, 0.14 mol) in toluene (250 ml.) was added dropwise methane sulfonic acid (13.7 ml_, 0.21 mol) and the reaction mixture was stirred at reflux temperature for 2 hours. The solvent was evaporated under reduce pressure and the residue was diluted with water and basified until pH=9 with an ammonium hydroxide solution. The formed precipitated was filtered and dried to give the title compound as a pale yellow solid (20.3 g, 60%). LC/MS: m/z 242 (M+H)⁺, Rt: 2.57 min.

References:

WO2009/56556,2009,A1 Location in patent:Page/Page column 35