1-Butanesulfonamide → 6-(1-n-Butanesulfonylcarbamoyl)-1-(2,4-dichlorobenzyl)-3-methyl-2-benzimidazolone

HRID 1699955Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1699955
[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[N:11]([CH3:12])[C:10](=[O:13])[N:9]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=3[Cl:22])[C:8]=2[CH:23]=1)([OH:3])=O.[CH2:24]([S:28]([NH2:31])(=[O:30])=[O:29])[CH2:25][CH2:26][CH3:27].C1CCN2C(=NCCC2)CC1>CN(C)C=O>[CH2:24]([S:28]([NH:31][C:1]([C:4]1[CH:5]=[CH:6][C:7]2[N:11]([CH3:12])[C:10](=[O:13])[N:9]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=3[Cl:22])[C:8]=2[CH:23]=1)=[O:3])(=[O:30])=[O:29])[CH2:25][CH2:26][CH3:27]

Komponenten

5

Edukt 3

HCID 184601-ButanesulfonamideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 223878516-Carboxy-1-(2,4-dichlorobenzyl)-3-methyl-2-benzimidazolone

Produkt 1

HCID 223877576-(1-n-Butanesulfonylcarbamoyl)-1-(2,4-dichlorobenzyl)-3-methyl-2-benzimidazoloneAusbeute 29,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

In the same manner as in Example 1, N,N′-carbonyldiimidazole (0.290 g) was added to a mixture of 6-carboxy-1-(2,4-dichlorobenzyl)-3-methyl-2-benzimidazolone (0.314 g) and N,N-dimethylformamide (9 ml), and the mixture was stirred at room temperature for 1 hr. 1-n-Butanesulfonamide (0.246 g) and DBU (0.273 g) were added and the mixture was stirred at 100° C. for 16 hr. The solvent was evaporated and the resulting mixture was extracted with chloroform and water. The organic layer was concentrated and the residue was purified by preparative thin layer chromatography to give 6-(1-n-butanesulfonylcarbamoyl)-1-(2,4-dichlorobenzyl)-3-methyl-2-benzimidazolone (0.123 g).

Aufarbeitung

  1. stirringthe mixture was stirred at 100° C. for 16 hr
  2. customThe solvent was evaporated
  3. extractionthe resulting mixture was extracted with chloroform and water
  4. concentrationThe organic layer was concentrated
  5. customthe residue was purified by preparative thin layer chromatography

Quellen und Nachweise

ORD-Eintrag
ord-d23aa593f1a24b49a951c0428c7c0baa
Quelldatensatz
uspto-grants-2002_02
Patentnummer
US06348474B1

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