Methyl iodide → HCID 13785432, compound

HRID 1905665Notes

Reaction equation

HRID 1905665 reaction equation
[OH:1][CH:2]1[N:6]([CH:7]2[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[C:5](=[O:13])[NH:4][C:3]1=[O:14].[CH3:15]I>CO.C[O-]>[OH:1][CH:2]1[N:6]([CH:7]2[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[C:5](=[O:13])[N:4]([CH3:15])[C:3]1=[O:14]

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 13785428HCID 13785428, compound

Product 1

HCID 13785432HCID 13785432, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3826051MethoxideSolvent

Procedure

2.0 g of 5-hydroxy-1-cyclohexylhydantoin were dissolved in 30 ml of methanol containing 600 mg of sodim methoxide. 20 minutes thereafter, 0.7 ml of methyl iodide were added dropwise to the solution and the reaction was continued at 50° C. for 1 hour. The solvent was removed by distillation and the residue was purified by thin layer chromatography on silica gel (ethyl acetate:hexane=1:1). The obtained crude product was recrystallized from benzene to give 500 mg of 5-hydroxy-1-cyclohexyl-3-methylhydantoin (compound 21) in the form of colorless needle crystals.

Workup

  1. customThe solvent was removed by distillation
  2. customthe residue was purified by thin layer chromatography on silica gel (ethyl acetate:hexane=1:1)
  3. customThe obtained crude product
  4. customwas recrystallized from benzene

Sources & evidence

ORD record
ord-78764aa5414242198ce3bf6bb70f4fa3
Source dataset
uspto-grants-1987_03
Patent number
US04647574

Reaction notes

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