Methyl iodide → HCID 54334135, compound

HRID 1885251Notes

Reaction equation

HRID 1885251 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-1-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-6bdde22c443f47ddaadd4cf2f8859683
Source dataset
uspto-grants-1992_09
Patent number
US05143928

Reaction notes

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