Water → HCID 178480057, compound

HRID 2396816Notes

Reaction equation

HRID 2396816 reaction equation
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]

Participants

6

Reactant 4

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

Product 1

HCID 178480057HCID 178480057, compoundYield 20.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-1851f08534554fbe90a79389835c4860
Source dataset
uspto-grants-1996_02
Patent number
US05494927

Reaction notes

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