Reaction #436679

Reaction equation

3-[(3-chloro-4-fluoro-benzimidoyl)-amino]-4-methoxy-benzoic acid methyl ester

NaOCl

Na2CO3

→

title compound

Yield 30.0%

2-(3-chloro-4-fluoro-phenyl)-7-methoxy-1H-benzoimidazole-4-carboxylic acid methyl ester

Yield 30.0%

Solvents

methanol

Conditions

Workup

1. 1
   Otherat room temperature
2. 2
   Temperaturerefluxed for 5 min
3. 3
   Extractionextracted with ethyl acetate
4. 4
   Concentrationthe extract was concentrated under a reduced pressure
5. 5
   OtherThe resulting residue was purified by silica gel column chromatography

Procedure

3-[(3-chloro-4-fluoro-benzimidoyl)-amino]-4-methoxy-benzoic acid methyl ester (3.24 g, 9.62 mmol) was dissolved in 50% methanol and 5% NaOCl (18 ml, 11.90 mmol) was added dropwise thereto at room temperature. After 5 min, Na2CO3 (2.04 g, 19.25 mmol) was added dropwise thereto and refluxed for 5 min. The resulting solution was cooled to room temperature, extracted with ethyl acetate, and the extract was concentrated under a reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound (0.95 g, 2.83 mmol) in a yield of 30%.

Source