Reaction #817398

Reaction equation

N-(2-aminophenyl)-4-chlorobenzenesulfonamide

benzo[b]thiophene-2-sulfonyl chloride

→

benzo[b]thiophene-2-sulfonic acid [2-(4-chlorobenzenesulfonylamino)phenyl]-amide

Yield 75.2%

Solvents

DCM

pyridine

DCM

Conditions

Workup

1. 1
   workup.ADDITIONwas added at RT
2. 2
   WashThe organic phase was washed with 10% HCl aqueous solution (5 mL), water (5 mL) and brine (5 mL)
3. 3
   DryingThe organic phase was dried over anhydrous sodium sulfate
4. 4
   Concentrationconcentrated under vacuum
5. 5
   OtherThe residue obtained
6. 6
   Otherwas purified by flash column chromatography
7. 7
   Washeluting with DCM/EtOAc

Procedure

To a solution of N-(2-aminophenyl)-4-chlorobenzenesulfonamide (0.5 mmol, prepared as in Example 11) in DCM (1 mL) and pyridine (1 mL), benzo[b]thiophene-2-sulfonyl chloride (0.55 mmol), prepared as above, was added at RT and the reaction mixture was then allowed to stir at RT overnight or until the reaction was complete as determined by TLC or LC-MS. The reaction mixture was then diluted with DCM (5 mL). The organic phase was washed with 10% HCl aqueous solution (5 mL), water (5 mL) and brine (5 mL). The organic phase was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue obtained was purified by flash column chromatography eluting with DCM/EtOAc to afford 180 mg of benzo[b]thiophene-2-sulfonic acid [2-(4-chlorobenzenesulfonylamino)phenyl]-amide. LC: Tr 1.23 min, MS: 479.8 (M+1)+.

Source