Benzimidazole → 1-(4'-Phenylsulfonylphenyl)benzimidazole

HRID 1668272

Reaktionsgleichung

Reaktionsgleichung von HRID 1668272
[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][CH:2]=1.[H-].[Na+].ClC1C=CC([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[S:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2C2C=CC(Cl)=CC=2)(=[O:27])=[O:26])=CC=1>CN(C=O)C>[C:20]1([S:25]([C:28]2[CH:33]=[CH:32][C:31]([N:1]3[C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=4[N:3]=[CH:2]3)=[CH:30][CH:29]=2)(=[O:27])=[O:26])[CH:19]=[CH:24][CH:23]=[CH:22][CH:21]=1

Komponenten

5

Edukt 3

HCID 5798BenzimidazoleHCID 24758Sodium hydride2×HCID 542057114-Chlorophenyl phenylsulfone

Produkt 1

HCID 668793591-(4'-Phenylsulfonylphenyl)benzimidazoleAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of benzimidazole (11.8 g, 0.10 mol) in DMF (500 ml) is added, at room temperature under nitrogen, sodium hydride (60% in mineral oil, 4.4 g, 0.11 mol), and the mixture is stirred for 10 min. The mixture is admixed with 4-chlorophenyl phenylsulfone (26.1 g, 0.10 mol) and stirred at 100° C. for 16 h. After again adding sodium hydride (60% in mineral oil, 2.0 g, 0.05 mol) at room temperature, the mixture is stirred at 130° C. for 16 h. After cooling to room temperature, the mixture is added to ice-water. Precipitated product is filtered off and washed with water. Yield: 91%.

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. filtrationPrecipitated product is filtered off
  3. washwashed with water

Quellen und Nachweise

ORD-Eintrag
ord-281a9fa326384db1b48a889046ecc214
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07989091B2

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