Acetic Acid → 3-[2-Butyl-4-chloro-1-(4-aminobenzyl)imidazol-5-yl] propenoic acid ethyl ester

HRID 466449Notes

Reaction equation

HRID 466449 reaction equation
[CH2:1]([O:3][C:4](=[O:27])[CH:5]=[CH:6][C:7]1[N:11]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=2)[C:10]([CH2:22][CH2:23][CH2:24][CH3:25])=[N:9][C:8]=1[Cl:26])[CH3:2].C(O)(=O)C>C(O)C.[Fe]>[CH2:1]([O:3][C:4](=[O:27])[CH:5]=[CH:6][C:7]1[N:11]([CH2:12][C:13]2[CH:14]=[CH:15][C:16]([NH2:19])=[CH:17][CH:18]=2)[C:10]([CH2:22][CH2:23][CH2:24][CH3:25])=[N:9][C:8]=1[Cl:26])[CH3:2]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 536609323-[2-Butyl-4-chloro-1-(4-nitrobenzyl)imidazol-5-yl]propenoic acid ethyl ester

Product 1

HCID 543706923-[2-Butyl-4-chloro-1-(4-aminobenzyl)imidazol-5-yl] propenoic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

A mixture of 0.5 g of 3-[2-butyl-4-chloro-1-(4-nitrobenzyl)imidazol-5-yl]propenoic acid ethyl ester (E isomer) prepared from Part B of Example 227, 1 g of iron and 2 mL of glacial acetic acid in 30 mL of absolute ethanol was refluxed for 1 hour. The reaction mixture was concentrated to dryness and the residue was dissolved in 50 mL of H2O. The aqueous solution was adjusted to pH 8 by K2CO3 and was extracted with ethyl acetate. The crude product obtained upon concentration of the ethyl acetate extract was purified by flash silica gel column chromatography (hexane:ethyl acetate=1:1 elution). The desired compound was obtained as a thick colorless oil, 0.35 g.

Workup

  1. temperaturewas refluxed for 1 hour
  2. concentrationThe reaction mixture was concentrated to dryness
  3. dissolutionthe residue was dissolved in 50 mL of H2O
  4. extractionwas extracted with ethyl acetate
  5. customThe crude product obtained upon concentration of the ethyl acetate
  6. extractionextract
  7. customwas purified by flash silica gel column chromatography (hexane:ethyl acetate=1:1 elution)

Sources & evidence

ORD record
ord-c23bf19c6c9848f6b055a707d9366a44
Source dataset
uspto-grants-1992_10
Patent number
US05155118

Reaction notes

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