Acetic Acid → HCID 13785431, compound

HRID 1905664Notes

Reaction equation

HRID 1905664 reaction equation
C[O-].[CH3:3][O:4][C:5](=O)[CH:6]=[O:7].[CH:9]1([NH:15][C:16]([NH2:18])=[O:17])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.C(O)(=O)C>CO>[CH3:3][O:4][CH:5]1[NH:18][C:16](=[O:17])[N:15]([CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[C:6]1=[O:7]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 69684CyclohexylureaHCID 86741332HCID 86741332, compound

Product 1

HCID 13785431HCID 13785431, compoundYield 31.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

750 mg of glyoxylic acid methyl ester methyl alcoholate and 920 mg of N-cyclohexylurea were refluxed in 50 ml of a mixture of acetic acid and methanol (4:1) for 1 hour. After cooling, the solvent was removed by distillation and the residue was purified by column chromatography on silica gel. The obtained crude product was recrystallized from benzene to give 420 mg of 5-methoxy-3-cyclohexylhydantoin (compound 20) in the form of colorless needle crystals.

Workup

  1. temperatureAfter cooling
  2. customthe solvent was removed by distillation
  3. customthe residue was purified by column chromatography on silica gel
  4. customThe obtained crude product
  5. customwas recrystallized from benzene

Sources & evidence

ORD record
ord-388adb4c598942939f19b7b3a97da9e7
Source dataset
uspto-grants-1987_03
Patent number
US04647574

Reaction notes

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