Ethanol → HCID 178480057, compound

HRID 486112Notes

Reaction equation

HRID 486112 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

HCID 178480057HCID 178480057, compoundYield 47.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-1,5-dihydro-1-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).

Workup

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

Sources & evidence

ORD record
ord-fca87508b6a64f1d9bae01926eb555c0
Source dataset
uspto-grants-1994_03
Patent number
US05290800

Reaction notes

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