Ethanol → HCID 178480057, Verbindung

HRID 2396818Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2396818
[CH3:1][C:2]([C:5]1[CH:6]=[C:7]([CH:16]=[C:17]2[N:21]([CH3:22])[C:20](SC)=[N:19][C:18]2=[O:25])[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])[CH3:3].Cl.[NH2:27][C:28]([NH2:30])=[NH:29].C(O)C.CC(C)([O-])C.[K+]>O>[CH3:1][C:2]([C:5]1[CH:6]=[C:7]([CH:16]=[C:17]2[N:21]([CH3:22])[C:20]([NH:29][C:28]([NH2:30])=[NH:27])=[N:19][C:18]2=[O:25])[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])[CH3:3]

Komponenten

6

Edukt 4

HCID 702EthanolHCID 5742Guanidine HydrochlorideHCID 23665647Potassium tert-butoxideHCID 54334135HCID 54334135, Verbindung

Produkt 1

HCID 178480057HCID 178480057, VerbindungAusbeute 47,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 5-[[3,5-bis(1,1-dimethylethyl)-4hydroxyphenyl]methylene]-1,5-dihydro-l-methyl-2-(methylthio)-4H-imidazol-4-one (3.0 g, 8 mmoles), guanidine hydrochloride (1.7 g, 18 mmoles) and 50 mL of ethanol is treated with potassium t-butoxide (1.5 g, 13 mmoles) and heated under reflux for 20 hours, then stirred into 400 mL of water. The precipitate is filtered off, rinsed with water, dried, and recrystallized from acetone to afford the product (1.4 g), mp 286°-287° C. (dec). A sample recrystallized from DMF/EtOH was analytically pure which is N-[5-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-4,5-dihydro-1-methyl-4-oxo-1H-imidazol-2-yl]guanidine, mp 288°-290° C. (dec).

Aufarbeitung

  1. temperatureheated
  2. temperatureunder reflux for 20 hours
  3. filtrationThe precipitate is filtered off
  4. washrinsed with water
  5. customdried
  6. customrecrystallized from acetone

Quellen und Nachweise

ORD-Eintrag
ord-283405f4d6504491b0b0b9e79fc7a9bf
Quelldatensatz
uspto-grants-1996_02
Patentnummer
US05494927

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