Methyl iodide → 5-(3,5-dichlorophenylthio)-1-methyl-4-isopropyl-2-(p-methoxybenzyloxymethyl)-1H-imidazole

HRID 1415995

Reaktionsgleichung

Reaktionsgleichung von HRID 1415995
[Cl:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[NH:14][C:13]([CH2:15][O:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=3)=[N:12][C:11]=2[CH:26]([CH3:28])[CH3:27])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[C:29](=O)([O-])[O-].[K+].[K+].CI>CN(C)C=O>[Cl:8][C:6]1[CH:5]=[C:4]([S:9][C:10]2[N:14]([CH3:29])[C:13]([CH2:15][O:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=3)=[N:12][C:11]=2[CH:26]([CH3:28])[CH3:27])[CH:3]=[C:2]([Cl:1])[CH:7]=1

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178491401HCID 178491401, Verbindung

Produkt 1

HCID 221305485-(3,5-dichlorophenylthio)-1-methyl-4-isopropyl-2-(p-methoxybenzyloxymethyl)-1H-imidazoleAusbeute 80,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

(5)In 25 ml of dry N,N-dimethylformamide was dissolved 11.0 g (25.1 mmol)of 5-(3,5-dichlorophenylthio)-4-isopropyl-2-(p-methoxybenzyloxymethyl)-1H-imidazole (16b), followed by addition of 5.2 g (38 mmol)of potassium carbonate powder. Then, 3.90 g (27.7 mmol)of methyl iodide was further added and the mixture was stirred at room temperature for 8 hours. This reaction mixture was concentrated under reduced pressure and the residue was diluted with water and extracted with diethyl ether. The organic layer was washed with water and dried over magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was fractionated by silica gel chromatography (ethyl acetate:methylene chloride=1:9). From the first fraction, 1.7 g (yield 15%)of the objective position isomer (17b')was obtained as oil. From the subsequent fraction, 9.14 g (yield 80%)of the objective 5-(3,5-dichlorophenylthio)-1-methyl-4-isopropyl-2-(p-methoxybenzyloxymethyl)-1H-imidazole (17b)was obtained. mp 79-80° C.

Aufarbeitung

  1. concentrationThis reaction mixture was concentrated under reduced pressure
  2. additionthe residue was diluted with water
  3. extractionextracted with diethyl ether
  4. washThe organic layer was washed with water
  5. dry with materialdried over magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customFrom the first fraction, 1.7 g (yield 15%)of the objective position isomer (17b')was obtained as oil

Quellen und Nachweise

ORD-Eintrag
ord-afec6b9e1c11450b9afb8aebc418a119
Quelldatensatz
uspto-grants-1999_06
Patentnummer
US05910506

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