Reaction #1093705

Reaction equation

5-chloroanthranilic acid methyl ester

pyridine

benzenesulfonylchloride

HCl

→

title compound

Methyl 2-phenylsulfonylamino-5-chlorobenzoate

Solvents

methylene chloride

Conditions

Workup

1. 1
   Extractionextracted with ethyl acetate
2. 2
   WashThe organic layer was washed
3. 3
   Otherdried over and
4. 4
   Concentrationconcentrated under reduced pressure
5. 5
   OtherThe residue was purified on silica gel column chromatography (hexane-AcOEt)

Procedure

To a solution of 5-chloroanthranilic acid methyl ester (400 mg; prepared in Reference Example 1) and pyridine (0.87 ml) in methylene chloride, benzenesulfonylchloride (0.33 ml) was added at 0° C. The solution was stirred overnight at room temperature. The reaction mixture was poured into diluted HCl and extracted with ethyl acetate. The organic layer was washed, dried over and concentrated under reduced pressure. The residue was purified on silica gel column chromatography (hexane-AcOEt) to give the title compound (664 mg) having the following physical data.

Source