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Methyl iodide → 5-(3-Chloro-5-trifluoromethylpyridin-2-yl)-3-methyl-1-(1-methylethyl)benzimidazol-2-one

HRID 1276081
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1276081
[H-].[Na+].[Cl:3][C:4]1[C:5]([C:14]2[CH:26]=[CH:25][C:17]3[N:18]([CH:22]([CH3:24])[CH3:23])[C:19](=[O:21])[NH:20][C:16]=3[CH:15]=2)=[N:6][CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1.[CH3:27]I>CN(C)C=O>[Cl:3][C:4]1[C:5]([C:14]2[CH:26]=[CH:25][C:17]3[N:18]([CH:22]([CH3:23])[CH3:24])[C:19](=[O:21])[N:20]([CH3:27])[C:16]=3[CH:15]=2)=[N:6][CH:7]=[C:8]([C:10]([F:11])([F:12])[F:13])[CH:9]=1
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Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 221148555-(3-Chloro-5-trifluoromethylpyridin-2yl)-1-(1-methylethyl)benzimidazol-2-one

Produkt 1

HCID 221148405-(3-Chloro-5-trifluoromethylpyridin-2-yl)-3-methyl-1-(1-methylethyl)benzimidazol-2-oneAusbeute 80,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel
2×

Versuchsvorschrift

0.23 g of an 80% strength by weight suspension of sodium hydride in mineral oil was added at 23° C. to 25 ml of anhydrous dimethylformamide. The mixture was then treated dropwise with a solution of 2.50 g of 5-(3-chloro-5-trifluoromethylpyridin-2-yl)-1-(1-methylethyl)benzimidazol-2-one in 25 ml of dimethylformamide and, after stirring for 15 minutes, with 1.05 g of methyl iodide. After stirring for 6 hours, the reaction mixture was poured into 300 ml of ice water. The aqueous phase was extracted three times with 100 ml of tert-butyl methyl ether each time, after which the combined organic phases were washed twice with 50 ml of water each time, dried over sodium sulfate and concentrated. Chromatography on silica gel using cyclohexane/ethyl acetate (4:1) as the eluent gave 2.1 g of colorless crystals. Yield: 75%; m.p.: 108-109° C.

Aufarbeitung

  1. extractionThe aqueous phase was extracted three times with 100 ml of tert-butyl methyl ether each time
  2. washafter which the combined organic phases were washed twice with 50 ml of water each time
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-89d3a59ec259467bac3a8888db981c72
Quelldatensatz
uspto-grants-2000_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06165941

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