2-Amino-3,4,6-trifluorobenzenethiol → Methyl 3-[(4,5,7-trifluorobenzothiazol-2-yl)methyl]phenylacetate

Participants

Reaction Conditions

Reaction Steps

To a solution of monomethyl 1,3-phenylene diacetate (531 mg, 2.6 mmol) in benzene (5 ml) was gradually added thionyl chloride (607 mg, 5.2 mmol). The mixture was heated to reflux for 2 hours. An excess of thionyl chloride was then distilled off in vacuo leaving 3-methoxycarbonylmethylphenylacetyl chloride. 2-Amino-3,4,6-trifluorothiophenol (507 mg, 2.8 mmol) was dissolved in N-methylpyrrolidone (NMP, 5 ml) under a nitrogen stream. To the resultant solution was gradually added the product 3-methoxycarbonylmethylphenylacetyl chloride thus obtained and the mixture was stirred at 100° C. for 2 hours. After cooling, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was dried and then evaporated to yield a residue, which was purified on a silica gel column to give methyl 3-[(4,5,7-trifluorobenzothiazol-2-yl)methyl]phenylacetate (267 mg, 27%) as an oil.

Provenance & Evidence