Water → 2-(2,6-dichlorophenyl)-1-methyl-1H-benzoimidazole-5-carboxylic acid ethyl ester

HRID 1514920

Reaktionsgleichung

Reaktionsgleichung von HRID 1514920
[CH2:1]([O:3][C:4](=[O:14])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][CH3:12])=[C:7]([NH2:13])[CH:6]=1)[CH3:2].[Cl:15][C:16]1[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[C:17]=1[CH:18]=O.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.[Yb+3].O>CS(C)=O.CCOC(C)=O>[CH2:1]([O:3][C:4]([C:5]1[CH:10]=[CH:9][C:8]2[N:11]([CH3:12])[C:18]([C:17]3[C:16]([Cl:15])=[CH:23][CH:22]=[CH:21][C:20]=3[Cl:24])=[N:13][C:7]=2[CH:6]=1)=[O:14])[CH3:2]

Komponenten

7

Edukt 4

HCID 962WaterHCID 67372,6-DichlorobenzaldehydeHCID 2733225Ytterbium triflate2×HCID 2824047Ethyl 3-amino-4-(methylamino)benzoate

Produkt 1

HCID 669657182-(2,6-dichlorophenyl)-1-methyl-1H-benzoimidazole-5-carboxylic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 3-amino-4-methylaminobenzoic acid ethyl ester (388 mg) and 2,6-dichlorobenzaldehyde (350 mg) in DMSO (4 mL) was added Yb(OTf)3 (50 mg) and the solution was stirred at room temperature for 24 h. More Yb(OTf)3 was added and stirring was continued for 24 h. This process was repeated another two times. The reaction mixture was partioned between water and EtOAc. The aqueous layer was extracted with EtOAc. The combined organic layers were dried, filtered and concentrated. The residue was purified by flash chromatography using a gradient of ethyl acetate/CH2Cl2 (0% to 25%) to give 2-(2,6-dichlorophenyl)-1-methyl-1H-benzoimidazole-5-carboxylic acid ethyl ester as a beige solid, mp=164-166° C.; MS (m/z) 349 (M+1).

Aufarbeitung

  1. stirringstirring
  2. waitwas continued for 24 h
  3. extractionThe aqueous layer was extracted with EtOAc
  4. customThe combined organic layers were dried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-a86591ff71ae44ff9e46f9b495c8a473
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08222248B2

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