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

HRID 345521

Reaktionsgleichung

Reaktionsgleichung von HRID 345521
[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

Komponenten

6

Edukt 4

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

Produkt 1

HCID 13423940Ethyl 4-(1H-imidazol-1-yl)benzoateAusbeute 33,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-30bea23f83bd45a6a20762b1f619e7ef
Quelldatensatz
uspto-grants-1991_10
Patentnummer
US05057525

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