Methyl iodide → HCID 54334135, compound

HRID 2396813Notes

Reaction equation

HRID 2396813 reaction equation
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>C(O)C.O>[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]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 81531DiisopropylethylamineHCID 53632063HCID 53632063, compound

Product 1

HCID 54334135HCID 54334135, compoundYield 69.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Iodomethane (1.2 mL, 19 mmols) is added to a stirred suspension of 5-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-1-methyl-2-thioxo-4-imidazolidinone (4.0 g, 12 mmols) and diisopropylethylamine (2.4 mL, 14 mmols) in ethanol (50 ml) and the mixture is stirred under an inert atmosphere at room temperature. After 18 hours the mixture is stirred in water (300 mL) for an hour and the product is filtered off, washed three times with water, and dried. Recrystallization from ethyl acetate gave the pure 5-[[3,5-Bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-1,5-dihydro-1-methyl-2-(methylthio)-4H-imidazol-4-one (3.0 g), mp 177°-179° C., retaining 0.25 equivalents of solvent of crystallization.

Workup

  1. filtrationthe product is filtered off
  2. washwashed three times with water
  3. customdried
  4. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-b754603c9a7141c7985e51f014ad4f1d
Source dataset
uspto-grants-1996_02
Patent number
US05494927

Reaction notes

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