Benzenesulfonamide → 6-Benzenesulfonylcarbamoyl-1-(2-chlorobenzyl)-2-methylbenzimidazole

HRID 276043

Reaktionsgleichung

Reaktionsgleichung von HRID 276043
[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[N:11]=[C:10]([CH3:12])[N:9]([CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[Cl:20])[C:8]=2[CH:21]=1)([OH:3])=O.[C:22]1([S:28]([NH2:31])(=[O:30])=[O:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C1(C2CCCCCCCCCC=2)CCCCCCCCNN=1>CN(C)C=O>[C:22]1([S:28]([NH:31][C:1]([C:4]2[CH:5]=[CH:6][C:7]3[N:11]=[C:10]([CH3:12])[N:9]([CH2:13][C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=4[Cl:20])[C:8]=3[CH:21]=2)=[O:3])(=[O:30])=[O:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Komponenten

5

Edukt 3

HCID 7370BenzenesulfonamideHCID 186808176-Carboxy-1-(2-Chlorobenzyl)-2-MethylbenzimidazoleHCID 536302743-(Cycloundecen-1-yl)-1,2-diazacycloundec-2-ene

Produkt 1

HCID 179386716-Benzenesulfonylcarbamoyl-1-(2-chlorobenzyl)-2-methylbenzimidazoleAusbeute 50,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

N,N′-carbonyldiimidazole (0.973 g) was added to a solution of 0.902 g of 6-carboxy-1-(2-chlorobenzyl)-2-methylbenzimidazole in 20 ml of N,N-dimethylformamide, and the mixture was stirred at room temperature for 1 hour. Subsequently, a solution of 0.943 g of benzenesulfonamide and 0.913 g of diazabicycloundecene in 5 ml of N,N-dimethylformamide was added thereto, and the mixture was stirred at 100° C. for 70 hours. The reaction solution was cooled, and the solvent was distilled off under reduced pressure. Water and chloroform were added to the residue, and 10% hydrochloric acid was added thereto while being stirred until the aqueous layer was acidified. The mixed solution was extracted twice with chloroform. The resulting organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate, and the solvent was distilled off under reduced pressure. The residue was dissolved in a small amount of chloroform, and ethyl acetate was added to the solution for crystallization. The crystals were separated through filtration, and were dried to give 0.667 g of 6-benzenesulfonylcarbamoyl-1-(2-chlorobenzyl)-2-methylbenzimidazole (163).

Aufarbeitung

  1. stirringthe mixture was stirred at 100° C. for 70 hours
  2. temperatureThe reaction solution was cooled
  3. distillationthe solvent was distilled off under reduced pressure
  4. additionWater and chloroform were added to the residue, and 10% hydrochloric acid
  5. additionwas added
  6. stirringwhile being stirred until the aqueous layer
  7. extractionThe mixed solution was extracted twice with chloroform
  8. washThe resulting organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate
  9. distillationthe solvent was distilled off under reduced pressure
  10. dissolutionThe residue was dissolved in a small amount of chloroform, and ethyl acetate
  11. additionwas added to the solution for crystallization
  12. customThe crystals were separated through filtration
  13. customwere dried

Quellen und Nachweise

ORD-Eintrag
ord-ea1883eb1a1345c9966a533520c85d86
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06352985B1

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