Réaction #7071

Équation de réaction

TsOH

5-bromothiophene-2-sulfonamide

4-bromo-2-chlorobenzoic acid

→

title compound

N-[4-bromo-2-chlorobenzoyl]-5-bromothiophene-2-sulfonamide

Solvants

dichloromethane

dichloromethane

Conditions de réaction

Traitement

1. 1
   AutreAn 8 mL reaction
2. 2
   workup.ADDITIONis added
3. 3
   Autrethe vial is capped
4. 4
   FiltrationAfter about 18 hr the reaction mixture is filtered
5. 5
   Concentrationconcentrated under reduced pressure
6. 6
   workup.ADDITIONcontaining product
7. 7
   Concentrationconcentrated

Mode opératoire

An 8 mL reaction vial is charged with 4-bromo-2-chlorobenzoic acid (0.39 mmol, 1.5 eq) and 2.0 mL of dichloromethane. A stock solution (4.0 mL) containing 5-bromothiophene-2-sulfonamide (0.26 mmol, 1 eq) and N,N-[dimethyl]-4-aminopyridine (48 mg, 0.39 mmol, 1.5 eq) in dichloromethane is added, followed by 0.261 g carbodiimide polystyrene resin (2.0 mmol/g, 0.52 mmol, 2.0 eq, Novabiochem) and the vial is capped and shaken. After 72 hr, 0.77 g sulphonated polystyrene resin (MP-TsOH) is added (1.53 mmol/g, 1.17 mmol, Argonaut). After about 18 hr the reaction mixture is filtered and concentrated under reduced pressure. Chromatography was applied to the residue and fractions containing product were combined and concentrated under reduce pressure to provide the title compound.

Source