Tetrahydrofuran → Ethyl 5-(2,4-dichlorophenyl)-4-imidazoly-5-oxopentanoate

HRID 31810Notes

Reaction equation

HRID 31810 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:16])[CH2:10][C:11]1[NH:12][CH:13]=[CH:14][N:15]=1.C1COCC1.[OH-].[K+].[C:24]([O:28][CH2:29][CH3:30])(=[O:27])[CH:25]=[CH2:26]>O.C(O)C>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:16])[CH:10]([C:11]1[NH:15][CH:14]=[CH:13][N:12]=1)[CH2:26][CH2:25][C:24]([O:28][CH2:29][CH3:30])=[O:27]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 8821Ethyl AcrylateHCID 14797Potassium HydroxideHCID 221427181-(2,4-dichlorophenyl)-2-(1H-imidazol-2-yl)ethanone

Product 1

HCID 57107536Ethyl 5-(2,4-dichlorophenyl)-4-imidazoly-5-oxopentanoateYield 108%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

1-(2,4-dichlorophenyl)-2-imidazolylethan-1-one (0.80 M) was dissolved with heating as necessary in a stirred mixture of THF (250 ml) and abs. ethanol (250 ml). After cooling to room temperature, potassium hydroxide (0.20 M) was added followed by a dropwise addition of ethyl acrylate (45.8 ml) via addition funnel over 10 min. A room temperature water bath was used to cool the exothermic reaction for the first 30 min. After stirring for 14-16 hours, the reaction was neutralized with gla. acetic acid (10 ml) and concentrated under reduced pressure. The residual dark reddish black slurry was dissolved in abs. ethanol (100 ml) and concentrated again under reduced pressure giving ethyl 5-(2,4-dichlorophenyl)-4-imidazolyl-5-oxopentanoate (2) in 108% yield. The crude material is contaminated with potassium salts and is used without further purification.

Workup

  1. temperaturewith heating as
  2. temperatureto cool
  3. customthe exothermic reaction for the first 30 min
  4. concentrationacetic acid (10 ml) and concentrated under reduced pressure
  5. dissolutionThe residual dark reddish black slurry was dissolved in abs
  6. concentrationethanol (100 ml) and concentrated again under reduced pressure

Sources & evidence

ORD record
ord-08c87bedadef47a7972279a69ae7c728
Source dataset
uspto-grants-2008_09
Patent number
US07425557B2

Reaction notes

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