p-Toluenesulfonic acid → N-[4-bromo-2-chlorobenzoyl]-5-bromothiophene-2-sulfonamide

HRID 1297179Notes

Reaction equation

HRID 1297179 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([Cl:11])[CH:3]=1.[Br:12][C:13]1[S:17][C:16]([S:18]([NH2:21])(=[O:20])=[O:19])=[CH:15][CH:14]=1.CC1C=CC(S(O)(=O)=O)=CC=1>ClCCl>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:21][S:18]([C:16]2[S:17][C:13]([Br:12])=[CH:14][CH:15]=2)(=[O:20])=[O:19])=[O:8])=[C:4]([Cl:11])[CH:3]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 1088294-Bromo-2-chlorobenzoic acidHCID 12413045-Bromo-2-thiophenesulfonamide

Product 1

HCID 22019517N-[4-bromo-2-chlorobenzoyl]-5-bromothiophene-2-sulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

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 reduced pressure to provide the title compound.

Workup

  1. customAn 8 mL reaction
  2. additionis added
  3. customthe vial is capped
  4. filtrationAfter about 18 hr the reaction mixture is filtered
  5. concentrationconcentrated under reduced pressure
  6. additioncontaining product
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-580c9d00c6cd47ceb84475476bc6b7b8
Source dataset
uspto-grants-2007_07
Patent number
US07250430B2

Reaction notes

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