Reaction #817422

Reaction equation

4-fluorobenzene-1,2-diamine

benzothiophene-2-sulfonyl chloride

→

N,N′-(4-fluoro-1,2-phenylene)bis(1-benzothiophene-2-sulfonamide)

Yield 37.0%

Solvents

DCM

pyridine

DCM

Conditions

Workup

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

Procedure

To a solution of 4-fluorobenzene-1,2-diamine (1 mmol) in DCM (2 mL) and pyridine (2 mL) at 0° C., benzothiophene-2-sulfonyl chloride (2.2 mmol) was added in small portions. The reaction mixture was then stirred at rt until the reaction was complete as determined by TLC or LC-MS. The reaction mixture was then diluted with DCM (15 mL). The organic phase was washed with 10% aqueous HCl (5 mL), water (5 mL), and 5 mL of brine. 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 obtain 192 mg of N,N′-(4-fluoro-1,2-phenylene)bis(1-benzothiophene-2-sulfonamide) as a solid.

Source