Urea, N-hexyl- → HCID 13785424, compound

HRID 1905663Notes

Reaction equation

HRID 1905663 reaction equation
C([O-])C1C=CC=CC=1.C([O:16][C:17](=O)[CH:18]=[O:19])C1C=CC=CC=1.[CH2:21]([NH:27][C:28]([NH2:30])=[O:29])[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]>C(O)(=O)C>[OH:19][CH:18]1[N:27]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[C:28](=[O:29])[NH:30][C:17]1=[O:16]

Participants

4

Reactant 2

HCID 75092Urea, N-hexyl-HCID 86741331HCID 86741331, compound

Product 1

HCID 13785424HCID 13785424, compoundYield 10.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

21.0 g of glyoxylic acid benzyl ester benzyl alcoholate and 10.0 g of N-hexylurea were refluxed in an 80% aqueous solution of acetic acid for 1.5 hours. After cooling, the reaction mixture was evaporated to dryness under reduced pressure. The obtained crude product was purified by column chromatography on silica gel (ethyl acetate:hexane=1:1) and was recrystallized from benzene to give 1.4 g of 5-hydroxy-1-hexylhydantoin (compound 12) in the form of colorless needle crystals.

Workup

  1. temperatureAfter cooling
  2. customthe reaction mixture was evaporated to dryness under reduced pressure
  3. customThe obtained crude product
  4. customwas purified by column chromatography on silica gel (ethyl acetate:hexane=1:1)
  5. customwas recrystallized from benzene

Sources & evidence

ORD record
ord-53ceacc40b434f2cabd402f57a26b83e
Source dataset
uspto-grants-1987_03
Patent number
US04647574

Reaction notes

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