Benzenesulfonyl chloride, 3,4-dichloro- → 1-(3,4-Dichloro-benzenesulfonyl)-1H-indole-2-carboxylic acid methyl ester

HRID 1595457

Reaktionsgleichung

Reaktionsgleichung von HRID 1595457
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([O:12][CH3:13])=[O:11].[H-].[Na+].[Cl:16][C:17]1[CH:18]=[C:19]([S:24](Cl)(=[O:26])=[O:25])[CH:20]=[CH:21][C:22]=1[Cl:23]>CN(C=O)C>[Cl:16][C:17]1[CH:18]=[C:19]([S:24]([N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH:3]=[C:2]2[C:10]([O:12][CH3:13])=[O:11])(=[O:25])=[O:26])[CH:20]=[CH:21][C:22]=1[Cl:23]

Komponenten

5

Edukt 3

HCID 7383Benzenesulfonyl chloride, 3,4-dichloro-HCID 24758Sodium hydrideHCID 70992Methyl 1H-indole-2-carboxylate

Produkt 1

HCID 217050871-(3,4-Dichloro-benzenesulfonyl)-1H-indole-2-carboxylic acid methyl esterAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Methyl indole-2-carboxylate (0.15 g) was dissolved in DMF and sodium hydride (41 mg) was added in a single portion. The reaction was stirred for 1 hour, then 3,4-dichlorobenzenesulphonyl chloride (0.25 g) was added in a single portion. Stirring was continued for a further 2 hours and then the reaction was quenched by the addition of water. The reaction mixture was partitioned between water and ethyl acetate. Combined organic extracts were dried (MgSO4) and concentrated in vacuo and the residue purified by column chromatography using isohexane-5% ethyl acetate as eluent to give the desired end product as a solid (51%). NMR δ (CDCl3) 3.96 (s, 3H), 7.22-8.20 (m, 8H); M/z (+) 384 (MH+), 352, 175.

Aufarbeitung

  1. stirringStirring
  2. waitwas continued for a further 2 hours
  3. customthe reaction was quenched by the addition of water
  4. customThe reaction mixture was partitioned between water and ethyl acetate
  5. dry with materialCombined organic extracts were dried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customthe residue purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-68781318143040b78dcc54e5d3867522
Quelldatensatz
uspto-grants-2001_09
Patentnummer
US06288103B1

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