Reaktion #7071

Reaktionsgleichung

TsOH

5-bromothiophene-2-sulfonamide

4-bromo-2-chlorobenzoic acid

→

title compound

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

Lösungsmittel

dichloromethane

dichloromethane

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle