Water → 6-Benzenesulfonylaminomethyl-1-(2-chlorobenzyl)-2-methylbenzimidazole

HRID 1276923Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1276923
[C:1]1([S:7]([NH2:10])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Cl.[Cl:14][C:15]1[CH:33]=[CH:32][CH:31]=[CH:30][C:16]=1[CH2:17][N:18]1[C:22]2[CH:23]=[C:24]([CH2:27]Cl)[CH:25]=[CH:26][C:21]=2[N:20]=[C:19]1[CH3:29].O>CN(C)C=O>[C:1]1([S:7]([NH:10][CH2:27][C:24]2[CH:25]=[CH:26][C:21]3[N:20]=[C:19]([CH3:29])[N:18]([CH2:17][C:16]4[CH:30]=[CH:31][CH:32]=[CH:33][C:15]=4[Cl:14])[C:22]=3[CH:23]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 7370BenzenesulfonamideHCID 24758Sodium hydrideHCID 226203411h-Benzimidazole,6-(chloromethyl)-1-[(2-chlorophenyl)methyl]-2-methyl-,hydrochloride

Produkt 1

HCID 226203396-Benzenesulfonylaminomethyl-1-(2-chlorobenzyl)-2-methylbenzimidazoleAusbeute 29,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 0.667 g of benzenesulfonic acid amide in 5 ml of N,N-dimethylformamide were added 0.127 g of 60% sodium hydride at room temperature, and the mixture was stirred for 1 hour. Further, 0.648 g of 1-(2-chlorobenzyl)-6-chloromethyl-2-methylbenzimidazole hydrochloride were added thereto, and the mixture was stirred at room temperature for 18 hours. Water was added to the reaction solution to stop the reaction, and the solvent was distilled off under reduced pressure. The residue was extracted with ethyl acetate and with water. The organic layer was concentrated, and was purified through silica-gel column chromatography (eluent: ethyl acetate) to give 0.240 g of 6-benzenesulfonylaminomethyl-1-(2-chlorobenzyl)-2-methylbenzimidazole (264).

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature for 18 hours
  2. customthe reaction
  3. distillationthe solvent was distilled off under reduced pressure
  4. extractionThe residue was extracted with ethyl acetate and with water
  5. concentrationThe organic layer was concentrated
  6. customwas purified through silica-gel column chromatography (eluent: ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-8816923f25664e078c386dcdb54756cb
Quelldatensatz
uspto-grants-2000_12
Patentnummer
US06166219

Notizen zur Reaktion

Wird geladen…