Sodium Chloride → 1-[(4-bromophenyl)sulfonyl]-1H-indole-2-carbaldehyde

HRID 2264627Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2264627
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[C:12]2[CH2:20][OH:21])(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(N(CC)CC)C.[Cl-].[Na+]>ClCCCl.CS(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[C:12]2[CH:20]=[O:21])(=[O:9])=[O:10])=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 5234Sodium ChlorideHCID 8471TriethylamineHCID 67044165{1-[(4-bromophenyl)sulfonyl]-1H-indol-2-yl}methanol

Produkt 1

HCID 442108071-[(4-bromophenyl)sulfonyl]-1H-indole-2-carbaldehydeAusbeute 98,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 111,2-DichloroethaneLösungsmittelHCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

To a solution of 0.93 g of {1-[(4-bromophenyl)sulfonyl]-1H-indol-2-yl}methanol and 1.1 mL of triethylamine in 10 mL of 1,2-dichloroethane, a solution of 1.21 g of sulfur trioxide-pyridine complex in 5 mL of DMSO was added under ice cooling, and the resulting mixture was stirred under ice cooling for 1 hour. The solution was poured into a mixed solution of 25 ml of ice water and 25 mL of saturated aqueous sodium chloride solution, the resulting mixture was extracted with 100 mL of ethyl acetate, the extract was washed with 5% aqueous potassium hydrogen sulfate solution, water and saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was washed with hexane to obtain 0.91 g of 1-[(4-bromophenyl)sulfonyl]-1H-indole-2-carbaldehyde as a beige solid. FAB+: 364, 366

Aufarbeitung

  1. extractionthe resulting mixture was extracted with 100 mL of ethyl acetate
  2. washthe extract was washed with 5% aqueous potassium hydrogen sulfate solution, water and saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. washThe residue was washed with hexane

Quellen und Nachweise

ORD-Eintrag
ord-a18ca397aefb404880692ac250803299
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07855225B2

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