Formaldehyde → HCID 54104549, compound

HRID 1461630Notes

Reaction equation

HRID 1461630 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:4]=[C:5]([NH:9][C:10](=[O:21])[CH:11]([NH:18][CH2:19][CH3:20])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:7][CH:8]=1.C=O.[C:26](=O)([O-])[O-].[K+].[K+]>CCCCCC.C(OCC)(=O)C>[CH2:19]([N:18]1[CH:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:10](=[O:21])[N:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:22])([F:23])[F:1])[CH:4]=2)[CH2:26]1)[CH3:20]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 11430Potassium CarbonateHCID 19978914HCID 19978914, compound

Product 1

HCID 54104549HCID 54104549, compoundYield 203.4%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

An ethanolic (50 mL) solution of the above N-aryl-2-ethylamino-2-phenylacetamide prepared in Example II (6.8 grams, 0.02 mol) and paraformaldehyde (0.65 grams, 0.02 mol) and potassium carbonate (1.5 grams, 0.01 mol) was heated under reflux for 2 hours. The reaction was followed by thin layer chromatography (3:1 hexane-ethyl acetate). The mixture was concentrated in a rotary evaporator. The product was extracted into ethyl acetate and washed with water and isolated to give the desired 1-ethyl-5-phenyl-3-(3-trifluoromethylphenyl) imidazolidine-4-one (6.8 grams, 97% yield) whose structure was confirmed by nuclear magnetic resonance, infra-red spectroscopy, and mass spectroscopy analysis.

Workup

  1. temperatureunder reflux for 2 hours
  2. concentrationThe mixture was concentrated in a rotary evaporator
  3. extractionThe product was extracted into ethyl acetate
  4. washwashed with water
  5. customisolated

Sources & evidence

ORD record
ord-0de9eff09ce04e34a5e3dc06882a5c0c
Source dataset
uspto-grants-1991_12
Patent number
US05076832

Reaction notes

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