4-Nitrobenzenesulfonamide → 1-(2-Chlorobenzyl)-2-methyl-6-(4-nitrobenzenesulfonylcarbamoyl)benzimidazole

HRID 1699618

Reaktionsgleichung

Reaktionsgleichung von HRID 1699618
[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.[N+:22]([C:25]1[CH:30]=[CH:29][C:28]([S:31]([NH2:34])(=[O:33])=[O:32])=[CH:27][CH:26]=1)([O-:24])=[O:23]>CN(C)C=O>[Cl:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[CH2:13][N:9]1[C:8]2[CH:21]=[C:4]([C:1](=[O:3])[NH:34][S:31]([C:28]3[CH:27]=[CH:26][C:25]([N+:22]([O-:24])=[O:23])=[CH:30][CH:29]=3)(=[O:33])=[O:32])[CH:5]=[CH:6][C:7]=2[N:11]=[C:10]1[CH3:12]

Komponenten

4

Edukt 2

HCID 227844-NitrobenzenesulfonamideHCID 186808176-Carboxy-1-(2-Chlorobenzyl)-2-Methylbenzimidazole

Produkt 1

HCID 186810031-(2-Chlorobenzyl)-2-methyl-6-(4-nitrobenzenesulfonylcarbamoyl)benzimidazoleAusbeute 43,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

N,N′-carbonyldiimidazole (0.432 g) is added all at once to an N,N-dimethylformamide (15 ml) solution of 6-carboxy-1-(2-chlorobenzyl)-2-methylbenzimidazole (0.432 g) (example 75), and the solution is stirred for one hour at room temperature. Subsequently, an N,N-dimethylformamide (5 ml) solution of 4-nitrobenzenesulfonamide (0.538 g) and diazabicyclotindecene (0.405 g) is added, and the solution is stirred for 84 hours at 100° C. The reaction solution is cooled and the solvent is removed through evaporation under reduced pressure. When chloroform and hydrochloric acid are added to the residue and the solution is stirred, crystals precipitated. The crystals are separated through filtration, dried, and thus, 1-(2-chlorobenzyl)-2-methyl-6-(4-nitrobenzenesulfonylcarbamoyl)benzimidazole (0.300 g) is obtained.

Aufarbeitung

  1. stirringthe solution is stirred for 84 hours at 100° C
  2. temperatureThe reaction solution is cooled
  3. customthe solvent is removed through evaporation under reduced pressure
  4. additionWhen chloroform and hydrochloric acid are added to the residue
  5. stirringthe solution is stirred
  6. customcrystals precipitated
  7. customThe crystals are separated through filtration
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-08d94b7200534d1ab77db94f0a2fe645
Quelldatensatz
uspto-grants-2002_02
Patentnummer
US06348032B1

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