p-Toluenesulfonic acid → HCID 10113563, compound

HRID 351124Notes

Reaction equation

HRID 351124 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([Br:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([NH2:22])(=[O:21])=[O:20])=[CH:15][CH:14]=1.CC1C=CC(S(O)(=O)=O)=CC=1>ClCCl>[Cl:1][C:2]1[CH:10]=[C:9]([Br:11])[CH:8]=[CH:7][C:3]=1[C:4]([NH:22][S:19]([C:16]1[CH:15]=[CH:14][C:13]([Cl:12])=[CH:18][CH:17]=1)(=[O:21])=[O:20])=[O:6]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 668244-ChlorobenzenesulfonamideHCID 1088294-Bromo-2-chlorobenzoic acid

Product 1

HCID 10113563HCID 10113563, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

An 8 mL reaction vial is charged with 2-chloro-4-bromobenzoic acid (0.39 mmol, 1.5 eq) and 2.0 mL of dichloromethane. A stock solution (4.0 mL) containing 4-chlorophenylsulfonamide (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 rotated. After 72 hr, 0.77 g sulphonated polystyrene resin (NP-TsOH) is added (1.53 mmol/g, 1.17 mmol, Argonaut). After about 18 hr the reaction mixture is filtered and concentrated under a stream of nitrogen. The residue is subjected to reverse phase HPLC; CombiPrep column, YMC ODS-A 20×50 mm column with 5 micron, C18, 120 Angstrom pore size, gradient: 5% to 95% CH3CN/0.01 HCl aqueous solution. Fractions containing product are 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 a stream of nitrogen
  6. additionFractions containing product
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8b069c504fc044a8ba9c6fd8aba1c7cf
Source dataset
uspto-grants-2007_02
Patent number
US07183320B2

Reaction notes

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