Benzenesulfonamide → HCID 9830227, compound

HRID 892285Notes

Reaction equation

HRID 892285 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.F[P-](F)(F)(F)(F)F.Br[P+](N1CCCC1)(N1CCCC1)N1CCCC1.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

8

Reactant 5

HCID 7370BenzenesulfonamideHCID 81531DiisopropylethylamineHCID 2733179PyBroPHCID 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 phosphoniumhexafluoro 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 an 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

Sources & evidence

ORD record
ord-a6f8f27e7a53417abcd7a144a467d1aa
Source dataset
uspto-grants-2006_02
Patent number
US07005538B1

Reaction notes

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