Methyl iodide → HCID 54334135, Verbindung

HRID 486107Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 486107
IC.[CH3:3][C:4]([C:7]1[CH:8]=[C:9]([CH:18]=[C:19]2[N:23]([CH3:24])[C:22](=[S:25])[NH:21][C:20]2=[O:26])[CH:10]=[C:11]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:12]=1[OH:13])([CH3:6])[CH3:5].[CH:27](N(C(C)C)CC)(C)C>C(O)C.O>[CH3:6][C:4]([C:7]1[CH:8]=[C:9]([CH:18]=[C:19]2[N:23]([CH3:24])[C:22]([S:25][CH3:27])=[N:21][C:20]2=[O:26])[CH:10]=[C:11]([C:14]([CH3:15])([CH3:16])[CH3:17])[C:12]=1[OH:13])([CH3:3])[CH3:5]

Komponenten

6

Edukt 3

HCID 6328Methyl iodideHCID 81531DiisopropylethylamineHCID 53632063HCID 53632063, Verbindung

Produkt 1

HCID 54334135HCID 54334135, VerbindungAusbeute 69,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

Iodomethane (1.2 mL, 19 mmols) is added to a stirred suspension of 5-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-1-methyl-2-thioxo-4-imidazolidinone (4.0 g, 12 mmols) and diisopropylethylamine (2.4 mL, 14 mmols) in ethanol (50 ml) and the mixture is stirred under an inert atmosphere at room temperature. After 18 hours the mixture is stirred in water (300 mL) for an hour and the product is filtered off, washed three times with water, and dried. Recrystallization from ethyl acetate gave the pure 5-[[3,5-Bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-1,5-dihydro-1-methyl-2-(methylthio)-4H-imidazol-4-one (3.0 g), mp 177°-179° C., retaining 0.25 equivalents of solvent of crystallization.

Aufarbeitung

  1. filtrationthe product is filtered off
  2. washwashed three times with water
  3. customdried
  4. customRecrystallization from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-086c69a95be14bf49699689087ac1545
Quelldatensatz
uspto-grants-1994_03
Patentnummer
US05290800

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