Acetic Acid → 3-[1-(4-Aminobenzyl)-2-butyl-4-chloroimidazol-5-yl]propen-1-ol

HRID 847093Notes

Reaction equation

HRID 847093 reaction equation
[N+:1]([C:4]1[CH:24]=[CH:23][C:7]([CH2:8][N:9]2[C:13]([CH2:14][CH:15]=[CH:16][OH:17])=[C:12]([Cl:18])[N:11]=[C:10]2[CH2:19][CH2:20][CH2:21][CH3:22])=[CH:6][CH:5]=1)([O-])=O.C(O)(=O)C>C(O)C.[Fe]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][N:9]2[C:13]([CH2:14][CH:15]=[CH:16][OH:17])=[C:12]([Cl:18])[N:11]=[C:10]2[CH2:19][CH2:20][CH2:21][CH3:22])=[CH:23][CH:24]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 665771703-[1-(4-Nitrobenzyl)-2-butyl-4-chloroimidazol-5-yl]propen-1-ol

Product 1

HCID 665771723-[1-(4-Aminobenzyl)-2-butyl-4-chloroimidazol-5-yl]propen-1-ol

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

A mixture of 0.2 g of 3-[1-(4-nitrobenzyl)-2-butyl-4-chloroimidazol-5-yl]propen-1-ol, 0.15 g of iron and 0.3 mL of glacial acetic acid in 10 mL of absolute ethanol was refluxed for 1 hour. The reaction mixture was concentrated to dryness and the residue was dissolved in 20 mL of water and the solution was made basic to pH 8 by adding K2CO3. The mixture was then extracted with ethyl acetate and the ethyl acetate layer was washed with water. The organic layer was concentrated to give a crude product which was purified by flash silica gel column chromatography (ethyl acetate elution). A pure product was obtained as an amorphous solid; NMR (200 MHz, CDCl3): δ 6.76 and 6.62 (dd, 4H, J=8.5 Hz); 6.42-6.22 (m, 2H); 2.57 (t, 2H, J=7.3 Hz); 1.65 (m, 2H); 1.33 (m, 2 H); 0.87 (t, 2H, J=7.3 Hz).

Workup

  1. temperaturewas refluxed for 1 hour
  2. concentrationThe reaction mixture was concentrated to dryness
  3. dissolutionthe residue was dissolved in 20 mL of water
  4. additionby adding K2CO3
  5. extractionThe mixture was then extracted with ethyl acetate
  6. washthe ethyl acetate layer was washed with water
  7. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-f6049172e5884c32977f323e53d74f49
Source dataset
uspto-grants-1992_08
Patent number
US05138069

Reaction notes

Loading…