HCID 19815428, compound → HCID 19815310, compound

HRID 465778Notes

Reaction equation

HRID 465778 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[N:5]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][CH:11]=2)[C:6]=1[CH2:7][OH:8]>CCO.C(O)(=O)C.[Fe]>[NH2:16][C:13]1[CH:12]=[CH:11][C:10]([CH2:9][N:5]2[C:6]([CH2:7][OH:8])=[C:2]([Cl:1])[N:3]=[C:4]2[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:15][CH:14]=1

Participants

5

Reactant 1

HCID 19815428HCID 19815428, compound

Product 1

HCID 19815310HCID 19815310, compoundYield 88.2%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

To a solution of 4-chloro-2-heptyl-5-hydroxymethyl-1-(4-nitrobenzyl)imidazole (1.00 g, 2.7 mmol) in EtOH (30 mL) and glacial acetic acid (5 mL) was added iron powder (2.5 g, 44.8 mmol). The mixture was stirred while being refluxed for 20 minutes. The solution was cooled, the iron was removed by filtration, and the solution was partitioned between EtOAc and 20% aq. K2CO3 (150 mL each). The organic phase was washed with saturated aqueous NaCl, dried (MgSO4), filtered and concentrated to afford 0.8 g yellow-orange oil. Flash chromatography (silica gel, 25 g; EtOAc/hexanes, 1:1) gave 0.74 g (80%) of yellow-orange oil. NMR (200 MHz, CDCl3) δ6.80-6.60 (ABq, 4H, 7 Hz, 32 Hz); 5.10 (s, 2H); 4.45 (s, 2H); 3.75-3.60 (m, 2H); 2.55 (t, 2H, 5 Hz); 1.75-1.65 (m, 2H); 1.30-1.15 (m, 8H); 0.90-0.80 (m, 3H). Mass Spec. 335.

Workup

  1. temperaturewhile being refluxed for 20 minutes
  2. temperatureThe solution was cooled
  3. customthe iron was removed by filtration
  4. customthe solution was partitioned between EtOAc and 20% aq. K2CO3 (150 mL each)
  5. washThe organic phase was washed with saturated aqueous NaCl
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-c22ebbe700cb446e9c8d7361dbeed087
Source dataset
uspto-grants-1992_10
Patent number
US05153197

Reaction notes

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