Water → HCID 178480057, Verbindung

HRID 486110Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 486110
Cl.[NH2:2][C:3]([NH2:5])=[NH:4].[CH3:6][C:7]([C:10]1[CH:11]=[C:12]([CH:21]=[C:22]2[N:26]([CH3:27])[C:25](SC)=[N:24][C:23]2=[O:30])[CH:13]=[C:14]([C:17]([CH3:20])([CH3:19])[CH3:18])[C:15]=1[OH:16])([CH3:9])[CH3:8].CC(C)([O-])C.[K+].O>C(O)C>[CH3:6][C:7]([C:10]1[CH:11]=[C:12]([CH:21]=[C:22]2[N:26]([CH3:27])[C:25]([NH:4][C:3]([NH2:5])=[NH:2])=[N:24][C:23]2=[O:30])[CH:13]=[C:14]([C:17]([CH3:20])([CH3:19])[CH3:18])[C:15]=1[OH:16])([CH3:9])[CH3:8]

Komponenten

6

Edukt 4

HCID 962WaterHCID 5742Guanidine HydrochlorideHCID 23665647Potassium tert-butoxideHCID 54334135HCID 54334135, Verbindung

Produkt 1

HCID 178480057HCID 178480057, VerbindungAusbeute 20,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Guanidine hydrochloride (1.7 g, 18 mmoles) is added to a mixture of 5-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene)-1,5-dihydro-1-methyl-2-(methylthio)-4-H-imidazole-4-one (3.0 g, 8 mmoles) and potassium tert-butoxide (1.5 g, 13 mmoles) in ethanol (50 mL), and stirred and heated to reflux under an inert atmosphere. After 24 hours the mixture is allowed to cool, and is poured into water (300 mL) and stirred. After half an hour the product is filtered off, rinsed three times with water and dried. Recrystallization from ethanol/DMF gave pure 5-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene)-4,5-dihydro-1-methyl-4-oxo-1H-imidazol-2-yl-guanidine (0.6 g), mp 288°-290° C. (dec).

Aufarbeitung

  1. temperatureheated
  2. temperatureto reflux under an inert atmosphere
  3. temperatureto cool
  4. stirringstirred
  5. filtrationAfter half an hour the product is filtered off
  6. washrinsed three times with water
  7. customdried
  8. customRecrystallization from ethanol/DMF

Quellen und Nachweise

ORD-Eintrag
ord-95b076f2cee64547affa77e86ee80bde
Quelldatensatz
uspto-grants-1994_03
Patentnummer
US05290800

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