Dimethylformamide → Methyl 2-(2,4-dichloro-6-methylphenoxy)-7-(1-ethylpropyl)-1-methyl-1H-benzimidazole-4-carboxylate

HRID 1698592Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1698592
Cl[C:2]1[N:6]([CH3:7])[C:5]2[C:8]([CH:16]([CH2:19][CH3:20])[CH2:17][CH3:18])=[CH:9][CH:10]=[C:11]([C:12]([O:14][CH3:15])=[O:13])[C:4]=2[N:3]=1.[Cl:21][C:22]1[CH:23]=[C:24]([CH3:30])[C:25]([OH:29])=[C:26]([Cl:28])[CH:27]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>C(=O)(O)[O-].[Na+]>[Cl:28][C:26]1[CH:27]=[C:22]([Cl:21])[CH:23]=[C:24]([CH3:30])[C:25]=1[O:29][C:2]1[N:6]([CH3:7])[C:5]2[C:8]([CH:16]([CH2:19][CH3:20])[CH2:17][CH3:18])=[CH:9][CH:10]=[C:11]([C:12]([O:14][CH3:15])=[O:13])[C:4]=2[N:3]=1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 152922,4-Dichloro-6-methylphenolHCID 67273217Methyl 2-chloro-7-(1-ethylpropyl)-1-methyl-1H-benzimidazole-4-carboxylate

Produkt 1

HCID 58012435Methyl 2-(2,4-dichloro-6-methylphenoxy)-7-(1-ethylpropyl)-1-methyl-1H-benzimidazole-4-carboxylateAusbeute 83,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 516892Sodium BicarbonateLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

A mixture of methyl 2-chloro-7-(1-ethylpropyl)-1-methyl-1H-benzimidazole-4-carboxylate (1.15 g, 3.90 mmol), 4,6-dichloro-o-cresol (2.07 g, 11.70 mmol), potassium carbonate (2.16 g, 15.60 mmol) and N,N-dimethylformamide (15 ml) was heated at 110° C. for 5 h. The residue was diluted with aqueous saturated sodium bicarbonate and extracted with ethyl acetate. The extracts were washed with water, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography on alumina with a 15% ethyl acetate/n-hexane to give 1.41 g (3.24 mmol, 83%) of the title compound as a white powder.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe extracts were washed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography on alumina with a 15% ethyl acetate/n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-01352fdf1a0a4a9f9656d47917b3ec6d
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08163935B2

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