Methyl iodide → HCID 54334135, compound

HRID 2396817Notes

Reaction equation

HRID 2396817 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.O1CCCC1>C(O)C>[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 4

HCID 6328Methyl iodideHCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 53632063HCID 53632063, compound

Product 1

HCID 54334135HCID 54334135, compoundYield 63.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of iodomethane (0.7 mL, 11 mmoles), 5-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-1-methyl-2-thioxo-4-imidazolidinone (2.5 g, 7 mmoles) and diisopropylethylamine (1.5 mL, 8.5 mmoles) in 25 mL of ethanol with enough tetrahydrofuran added to effect solution is stirred overnight under N2 at room temperature, then stirred into 250 mL of ice water. The precipitate is filtered off, rinsed with water, dried, and recrystallized from ethyl acetate to afford the product (1.6 g) 5-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-1,5-dihydro-l-methyl-2-(methylthio)-4H-imidazol-4-one, mp 177°-178° C., retaining 0.25 equivalent of solvent of recrystallization.

Workup

  1. additionadded to effect solution
  2. filtrationThe precipitate is filtered off
  3. washrinsed with water
  4. customdried
  5. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-6fe068a9ea9546e1b7f17e442c369822
Source dataset
uspto-grants-1996_02
Patent number
US05494927

Reaction notes

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