Acetic Acid → Methyl 1-(4-aminobenzyl)-2-butyl-4-chloroimidazole-5-acetate

HRID 465773Notes

Reaction equation

HRID 465773 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[CH:19][CH:18]=2)[C:7]([CH2:11][C:12]([O:14][CH3:15])=[O:13])=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4].C(O)(=O)C>[Fe].CO>[CH2:1]([C:5]1[N:6]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][CH:18]=2)[C:7]([CH2:11][C:12]([O:14][CH3:15])=[O:13])=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 15159734HCID 15159734, compound

Product 1

HCID 15356445Methyl 1-(4-aminobenzyl)-2-butyl-4-chloroimidazole-5-acetateYield 98.5%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Procedure

A mixture of methyl 2-butyl-4-chloro-1-(4-nitrobenzyl)imidazole-5-acetate (5.00 g, 13.7 mmol, 1 eq), iron (2.67 g, 47.8 mmol, 3.5 eq), glacial acetic acid (5.47 mL, 95.3 mmol, 7 eq), and methanol (250 mL) was refluxed for 5.5 hours. The solvent was removed by rotary evaporation. The residue was diluted with water (300 mL) and extracted five times with 300 mL portions of ethyl acetate. The organic layers were dried and concentrated. The residue was flash chromatographed in 75:25 hexane/ethyl acetate over silica gel to give 4.53 g of a golden yellow oil which crystallized after standing for several days. NMR (200 MHz, CDCl3) δ6.72 (d, 2H, J=7 Hz); 6.60 (d, 2H, J=7 Hz); 4.99 (s, 2H); 3.61 (s, 3H); 3.47 (s, 2H); 2.60 (t, 2H, J= 7 Hz); 1.68 (m, 2H); 1.35 (m, 2H); 0.86 (t, 3H, J=7 Hz). Mass spectrum shows M+=335/337. Mass Calcd. for C17H22N3O2Cl: 335.1400. Found: 335.1407.

Workup

  1. temperaturewas refluxed for 5.5 hours
  2. customThe solvent was removed by rotary evaporation
  3. additionThe residue was diluted with water (300 mL)
  4. extractionextracted five times with 300 mL portions of ethyl acetate
  5. customThe organic layers were dried
  6. concentrationconcentrated
  7. customchromatographed in 75:25 hexane/ethyl acetate over silica gel

Sources & evidence

ORD record
ord-0ed9a2772f9946519c4b01323f0a44d1
Source dataset
uspto-grants-1992_10
Patent number
US05153197

Reaction notes

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