Water → 5-Chloro-1,3-dihydro-1-(2-methoxy-4-nitrobenzenesulfonyl)-3-phenyl-2H-benzimidazol-2-one

HRID 1081478

Reaktionsgleichung

Reaktionsgleichung von HRID 1081478
[H-].[Na+].[Cl:3][C:4]1[CH:19]=[CH:18][C:7]2[NH:8][C:9](=[O:17])[N:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:6]=2[CH:5]=1.[CH3:20][O:21][C:22]1[CH:27]=[C:26]([N+:28]([O-:30])=[O:29])[CH:25]=[CH:24][C:23]=1[S:31](Cl)(=[O:33])=[O:32].O>CN(C=O)C>[Cl:3][C:4]1[CH:19]=[CH:18][C:7]2[N:8]([S:31]([C:23]3[CH:24]=[CH:25][C:26]([N+:28]([O-:30])=[O:29])=[CH:27][C:22]=3[O:21][CH3:20])(=[O:32])=[O:33])[C:9](=[O:17])[N:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:6]=2[CH:5]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 1086532H-Benzimidazol-2-one, 1,3-dihydro-6-chloro-1-phenyl-HCID 3094582-Methoxy-4-nitrobenzenesulfonyl chloride

Produkt 1

HCID 152290365-Chloro-1,3-dihydro-1-(2-methoxy-4-nitrobenzenesulfonyl)-3-phenyl-2H-benzimidazol-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

0.15 g of sodium hydride as an 80% dispersion in oil was added in portions, with stirring, to a solution of 1.223 g of 5-chloro-1,3-dihydro-3-phenyl-2H-benzimidazol-2-one in 12 ml of DMF at room temperature; 1.384 g of 2-methoxy-4-nitrobenzenesulfonyl chloride were then introduced and the reaction medium was stirred at room temperature for 24 hours. The solvent was then evaporated off under vacuum and the residue obtained was taken up with water. It was then extracted with DCM, washed with water and then dried over sodium sulfate and the solvent was evaporated off to dryness. The residue obtained was chromatographed on silica using a DCM/AcOEt mixture (92/8; v/v) as the eluent to give the expected product in the form of a yellow product, which crystallized from absolute EtOH. m=1.870 g. M.p.>250° C.

Aufarbeitung

  1. customThe solvent was then evaporated off under vacuum
  2. customthe residue obtained
  3. extractionIt was then extracted with DCM
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. customthe solvent was evaporated off to dryness
  7. customThe residue obtained
  8. customwas chromatographed on silica using a DCM/AcOEt mixture (92/8; v/v) as the eluent

Quellen und Nachweise

ORD-Eintrag
ord-653df082ff374065b37e59f089874a66
Quelldatensatz
uspto-grants-1996_12
Patentnummer
US05585394

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