Hydrochloric Acid → 3-(4-Fluorophenyl)-2-hydroxy-5,5-dimethyl-3,5-dihydro-4H-imidazol-4-one

HRID 224945Notes

Reaction equation

HRID 224945 reaction equation
CO[C:3](=[O:18])[C:4]([CH3:17])([CH3:16])[NH:5][C:6](=[O:15])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=1.Cl>CC(C)=O>[F:14][C:11]1[CH:10]=[CH:9][C:8]([N:7]2[C:3](=[O:18])[C:4]([CH3:16])([CH3:17])[NH:5][C:6]2=[O:15])=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 3054225Alanine, N-((p-fluorophenyl)carbamoyl)-2-methyl-, methyl ester

Product 1

HCID 30542273-(4-Fluorophenyl)-2-hydroxy-5,5-dimethyl-3,5-dihydro-4H-imidazol-4-one

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 17.2 g (67.5 mmol) of N-[(4-fluorophenyl)-carbamoyl]-2-methylalanine methyl ester in 150 ml of 6-N aqueous hydrochloric acid and 50 ml of acetone was warmed on a steam bath for 2 hours. The mixture was then concentrated. The product, which had precipitated was dried at 40°/15 Torr and then recrystallized from toluene. The recrystallized product was dried at 50° C. for 20 hours, under greatly reduced pressure, to yield 3-(4-fluorophenyl)-5,5-dimethylhydantoin, m.p. 166°-167° C.

Workup

  1. concentrationThe mixture was then concentrated
  2. customThe product, which had precipitated
  3. customwas dried at 40°/15 Torr
  4. customrecrystallized from toluene
  5. customThe recrystallized product was dried at 50° C. for 20 hours, under greatly reduced pressure

Sources & evidence

ORD record
ord-b60f5cc87b134a799e38f69e1866db4b
Source dataset
uspto-grants-1980_11
Patent number
US04234736

Reaction notes

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