Thionyl Chloride → HCID 25073245, compound

Participants

Reaction Steps

To 3-(2-hydroxy-6-(3-hydroxyphenyl)naphthalene-1-yl)benzoic acid (220 mg, 0.62 mmol, 1 eq), which is dissolved under a nitrogen atmosphere in 5 ml of dry DME, thionyl chloride (600 μl) is added, and the mixture is stirred at RT for 2 h. After the excess thionyl chloride has been removed in vacuum on a rotary evaporator, the residue is dissolved in dry THF and added dropwise to a suspension of 5-methyl-1,3,4-thiadiazole-2-amine (42.6 mg, 0.74 mmol, 1.2 eq) in dry dichloromethane cooled at 0° C. The reaction mixture is stirred at RT over night, followed by removing the solvent on a rotary evaporator. Purification of the raw product by column chromatography with dichloromethane/methanol 95/5 as the eluent yielded the desired compound in a yield of 47%, 132 mg.

Provenance & Evidence