Benzenesulfonamide → HCID 9830227, compound

HRID 2251713Notes

Reaction equation

HRID 2251713 reaction equation
[C:1]1([S:7]([NH2:10])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:11][C:12]1[CH:13]=[C:14]([CH:18]=[C:19]([Br:30])[C:20]=1[O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([Br:29])[CH:24]=1)[C:15](O)=[O:16].C(N(CC)C(C)C)(C)C.O.ON1C2C=CC=CC=2N=N1>CN(C)C=O.ClCCl>[Br:11][C:12]1[CH:13]=[C:14]([CH:18]=[C:19]([Br:30])[C:20]=1[O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([Br:29])[CH:24]=1)[C:15]([NH:10][S:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)(=[O:9])=[O:8])=[O:16]

Participants

7

Reactant 4

HCID 7370BenzenesulfonamideHCID 81531DiisopropylethylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 22242280HCID 22242280, compound

Product 1

HCID 9830227HCID 9830227, compoundYield 16%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent3×

Procedure

To a stirred mixture of benzenesulphonamide (0.89 mmol), dichloromethane (1 mL) and dimethylformamide (one drop), a solution of 3,5-dibromo-4-(3-bromo-benzyloxy)benzoic acid (0.17 mmol) and N,N-diisopropylethylamine (0.86 mmol) in dichloromethane (1 mL) was added. After 15 minutes bromotripyrrolidino phosphoniumlhexafluoro phosphate (0.21 mmol) and 1-hydroxybenzotriazole hydrate (0.045 mmol) were added. The reaction mixture was stirred at room temperature over night. Dichloromethane was added (3 mL) and the mixture was washed with an aqueous solution of citric acid (10%, 3×3 mL). The organic layer was washed with brine, dried over magnesium sulphate and concentrated in vacuo. The residue was purified on column (silica gel, chloroform/methanol 19:1) and further purified on semi-preparative HPLC (column and eluents as described for Examples 27, 28 and 30) to give 16 mg (16%) of N-[3,5-dibromo-4-(3-bromobenzyloxy)benzoyl]benzene-sulphonamide.

Workup

  1. washthe mixture was washed with an aqueous solution of citric acid (10%, 3×3 mL)
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified on column (silica gel, chloroform/methanol 19:1)
  6. customfurther purified on semi-preparative HPLC (column and eluents as described for Examples 27, 28 and 30)

Sources & evidence

ORD record
ord-974e0ce4a9a24c0cbab7caa303d5e1f0
Source dataset
uspto-grants-2008_01
Patent number
US07319163B2

Reaction notes

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