Methanol → 2-(2,6-dichloro-phenyl)-3H-benzoimidazole-5-sulfonic acid (3,4-dimethyl-phenyl)-amide

HRID 1514861Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1514861
[NH2:1][C:2]1[CH:3]=[C:4]([S:9]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[C:15]([CH3:20])[CH:14]=2)(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[NH2:8].[Cl:21][C:22]1[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[C:23]=1[CH:24]=O.CO>CS(C)=O>[CH3:20][C:15]1[CH:14]=[C:13]([NH:12][S:9]([C:4]2[CH:5]=[CH:6][C:7]3[N:8]=[C:24]([C:23]4[C:22]([Cl:21])=[CH:29][CH:28]=[CH:27][C:26]=4[Cl:30])[NH:1][C:2]=3[CH:3]=2)(=[O:11])=[O:10])[CH:18]=[CH:17][C:16]=1[CH3:19]

Komponenten

5

Edukt 3

HCID 887MethanolHCID 67372,6-DichlorobenzaldehydeHCID 669651143,4-diamino-N-(3,4-dimethyl-phenyl)-benzenesulfonamide

Produkt 1

HCID 669657082-(2,6-dichloro-phenyl)-3H-benzoimidazole-5-sulfonic acid (3,4-dimethyl-phenyl)-amide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

A freshly prepared solution of 3,4-diamino-N-(3,4-dimethyl-phenyl)-benzenesulfonamide in DMSO (0.2 M, 0.40 mL) was placed in a vial. To it was added 2,6-dichloro-benzaldehyde (0.2 M in toluene, 0.48 mL), followed by FeCl3 (0.02 M in THF, 0.2 mL). The mixture was stirred in open air at ambient temperature overnight. The mixture was then diluted by MeOH and the whole was loaded onto a solid phase extraction (SPE) cartridge that contained strong cation exchange (SCX) (1 g media in 6 mL cartridge, United Chemical Technology). Wash-to-waste (5 mL MeOH) was followed by elute-to-collect (5 mL 20:2:1 ethyl acetate-MeOH-Et3N) and, after evaporation of volatiles, the crude was further purified by silica gel column chromatography to give 2-(2,6-dichloro-phenyl)-3H-benzoimidazole-5-sulfonic acid (3,4-dimethyl-phenyl)-amide: MS (m/z) 446 (M+1).

Aufarbeitung

  1. extractionthe whole was loaded onto a solid phase extraction (SPE) cartridge that
  2. washWash-to-waste (5 mL MeOH)
  3. customby elute-to-collect (5 mL 20:2:1 ethyl acetate-MeOH-Et3N)
  4. customafter evaporation of volatiles
  5. customthe crude was further purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-47b4d584ed814ad2b112421bfc930cf6
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08222248B2

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