Imidazole → Ethyl 4-(1H-imidazol-1-yl)benzoate

HRID 1088329Notes

Reaction equation

HRID 1088329 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.F[C:7]1[CH:17]=[CH:16][C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:9][CH:8]=1.[I-].[K+].CN(C)C(=O)C>O>[N:1]1([C:7]2[CH:17]=[CH:16][C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:9][CH:8]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 4875Potassium IodideHCID 31374DimethylacetamideHCID 67976Benzoic acid, 4-fluoro-, ethyl ester

Product 1

HCID 13423940Ethyl 4-(1H-imidazol-1-yl)benzoateYield 33.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 13.6 parts of 1H-imidazole, 16.8 parts of ethyl 4-fluorobenzoate, 0.1 parts of potassium iodide and 54 parts of N,-N-dimethylacetamide was stirred and refluxed for 20 hours. The reaction mixture was cooled to room temperature and poured onto a lot of water. The product was extracted a few times with benzene. The combined extracts were washed thoroughly with water, dried, filtered and evaporated. The residue was stirred in hexane. The product was filtered off and dried, yielding 7.2 parts (33.3%) of ethyl 4-(1H-imidazol-1-yl)benzoate; mp. 100.3° C. (intermediate 18).

Workup

  1. temperaturerefluxed for 20 hours
  2. extractionThe product was extracted a few times with benzene
  3. washThe combined extracts were washed thoroughly with water
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. stirringThe residue was stirred in hexane
  8. filtrationThe product was filtered off
  9. customdried

Sources & evidence

ORD record
ord-23fcd1a70f06455397dc02c9713011c8
Source dataset
uspto-grants-1990_10
Patent number
US04962115

Reaction notes

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