Ethyl propiolate → ethyl 2-(4-chlorophenyl)-1H-imidazole-5-carboxylate

HRID 900240Notes

Reaction equation

HRID 900240 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([NH:8]O)=[NH:7])=[CH:4][CH:3]=1.[CH2:12]([O:14][C:15](=[O:18])[C:16]#[CH:17])[CH3:13]>CO>[CH2:12]([O:14][C:15]([C:16]1[NH:7][C:6]([C:5]2[CH:10]=[CH:11][C:2]([Cl:1])=[CH:3][CH:4]=2)=[N:8][CH:17]=1)=[O:18])[CH3:13]

Participants

4

Reactant 2

HCID 12182Ethyl propiolateHCID 178513302HCID 178513302, compound

Product 1

HCID 53440929ethyl 2-(4-chlorophenyl)-1H-imidazole-5-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
190 °C

Procedure

1.0 g (5.9 mmol) of 4-chloro-N-hydroxy-benzamidine and 776 mg (7.96 mmol) of propynoic acid ethyl ester were dissolved in methanol and the resulting solution was boiled under reflux for 15 h. The solvent was removed under reduced pressure, and the residue was dissolved in Dowtherm A. This solution was heated to 190° C. for 2.5 h, allowed to cool, then poured into n-heptane. The precipitated product was filtered off and washed with n-heptane.

Workup

  1. temperatureunder reflux for 15 h
  2. customThe solvent was removed under reduced pressure
  3. dissolutionthe residue was dissolved in Dowtherm A
  4. temperatureto cool
  5. additionpoured into n-heptane
  6. filtrationThe precipitated product was filtered off
  7. washwashed with n-heptane

Sources & evidence

ORD record
ord-689333cd43e344038eaa569e13ebac4f
Source dataset
uspto-grants-2008_04
Patent number
US07358268B2

Reaction notes

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