Reaction #817423

Reaction equation

4-cyanobenzene-1,2-diamine

benzothiophene-2-sulfonyl chloride

→

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

Yield 35.0%

Solvents

ethyl acetate

pyridine

Conditions

Workup

1. 1
   WashThe organic phase was washed with 10% aqueous HCl solution (15 mL), water (15 mL) and brine (5 mL)
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-cyanobenzene-1,2-diamine (1 mmol) in pyridine (4 mL), benzothiophene-2-sulfonyl chloride (2.2 mmol) was added in small portions. The reaction mixture was then heated at 80° C. with stirring until the reaction was complete as determined by TLC or LC-MS. The reaction mixture was then diluted with ethyl acetate (20 mL). The organic phase was washed with 10% aqueous HCl solution (15 mL), water (15 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 obtain 184 mg of N,N′-(4-cyano-1,2-phenylene)bis(1-benzothiophene-2-sulfonamide) as a solid.

Source