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

HRID 1857695

Reaktionsgleichung

Reaktionsgleichung von HRID 1857695
[CH2:1]([O:8][CH2:9][C:10]1[NH:11][C:12]([S:18][C:19]2[CH:24]=[C:23]([Cl:25])[CH:22]=[C:21]([Cl:26])[CH:20]=2)=[C:13]([CH:15]([CH3:17])[CH3:16])[N:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:27]I.[OH-].[Na+]>O1CCCC1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:1]([O:8][CH2:9][C:10]1[N:11]([CH3:27])[C:12]([S:18][C:19]2[CH:24]=[C:23]([Cl:25])[CH:22]=[C:21]([Cl:26])[CH:20]=2)=[C:13]([CH:15]([CH3:17])[CH3:16])[N:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 1784190342-Benzyloxymethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1H-imidazole

Produkt 1

HCID 221305032-benzyloxymethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazoleAusbeute 22 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

In 50 ml of dry tetrahydrofuran was dissolved 15 g (44 mmol) of 2-benzyloxymethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1H-imidazole (16a). To this solution was added 6.87 g (48.4 mmol) of methyl iodide under ice-cooling, further followed by addition of 1.94 g (48.4 mmol) of sodium hydroxide and 100 mg of tetrabutylammonium bromide. After the ice-water bath was removed, the mixture was stirred for 1 hour. This reaction mixture was concentrated under reduced pressure and the residue was neutralized with hydrochloric acid and sodium hydrogen carbonate to be weakly basic and extracted twice with ethyl acetate. The pooled organic layer was washed with water and dried over sodium sulfate. The solvent was then distilled off under reduced pressure and the residue was fractionated by silica gel chromatography (3% ethyl acetate in methylene chloride). From the first fraction, 3.5 g (yield 22%) of the objective position isomer (17a') was obtained as oil. From the subsequent fraction, 10.4 g (yield 67%) of the objective 2-benzyloxymethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazole (17a) was obtained as oil.

Aufarbeitung

  1. temperaturecooling
  2. customAfter the ice-water bath was removed
  3. concentrationThis reaction mixture was concentrated under reduced pressure
  4. extractionextracted twice with ethyl acetate
  5. washThe pooled organic layer was washed with water
  6. dry with materialdried over sodium sulfate
  7. distillationThe solvent was then distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-3dd2006a7aae42428919d3fbba9df829
Quelldatensatz
uspto-grants-2000_11
Patentnummer
US06147097

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