Methyl iodide → HCID 54334135, Verbindung

HRID 1885251Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1885251
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.O1CCCC1>C(O)C>[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 4

HCID 6328Methyl iodideHCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 53632063HCID 53632063, Verbindung

Produkt 1

HCID 54334135HCID 54334135, VerbindungAusbeute 63,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of iodomethane (0.7 mL, 11 mmoles), 5-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-1-methyl-2-thioxo-4-imidazolidinone (2.5 g, 7 mmoles) and diisopropylethylamine (1.5 mL, 8.5 mmoles) in 25 mL of ethanol with enough tetrahydrofuran added to effect solution is stirred overnight under N2 at room temperature, then stirred into 250 mL of ice water. The precipitate is filtered off, rinsed with water, dried, and recrystallized from ethyl acetate to afford the product (1.6 g) 5-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-1,5-dihydro-1-methyl-2-(methylthio)-4H-imidazol-4-one, mp 177°-178° C., retaining 0.25 equivalent of solvent of recrystallization.

Aufarbeitung

  1. additionadded to effect solution
  2. filtrationThe precipitate is filtered off
  3. washrinsed with water
  4. customdried
  5. customrecrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-6bdde22c443f47ddaadd4cf2f8859683
Quelldatensatz
uspto-grants-1992_09
Patentnummer
US05143928

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