methyl 4-[(2-butyl-5-formyl-4-iodo-1H-imidazol-1-yl)methyl]-2,3-dichlorobenzoate → methyl 4-[(2-butyl-5-formyl-1H-imidazol-1-yl)methyl]-2,3-dichlorobenzoate

HRID 37002Notes

Reaction equation

HRID 37002 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:13][C:14]2[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[C:16]([Cl:24])[C:15]=2[Cl:25])[C:7]([CH:11]=[O:12])=[C:8](I)[N:9]=1)[CH2:2][CH2:3][CH3:4]>[Pd].C(OCC)(=O)C.O>[CH2:1]([C:5]1[N:6]([CH2:13][C:14]2[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[C:16]([Cl:24])[C:15]=2[Cl:25])[C:7]([CH:11]=[O:12])=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 1

HCID 19936891methyl 4-[(2-butyl-5-formyl-4-iodo-1H-imidazol-1-yl)methyl]-2,3-dichlorobenzoate

Product 1

HCID 19936913methyl 4-[(2-butyl-5-formyl-1H-imidazol-1-yl)methyl]-2,3-dichlorobenzoateYield 96%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 34.2 g (0.069 mol) of methyl 4-[(2-butyl-5-formyl-4-iodo-1H-imidazol-1-yl)methyl]-2,3-dichlorobenzoate and 6.84 g of 10% palladium on carbon in 850 mL of ethyl acetate was shaken under hydrogen at 3 Torr for 1 hour. The mixture was filtered through Celite® and concentrated under vacuum to 300 mL. This solution was washed in turn with 5% sodium carbonate solution, water, and brine and then concentrated to an oil which crystallized on standing. This was dissolved in 25 mL of hot methanol which when cooled gave crystals. The suspension was slowly diluted with water and then filtered to give 24.39 g (96%) of crystals; mp 94°-96° C.

Workup

  1. filtrationThe mixture was filtered through Celite®
  2. concentrationconcentrated under vacuum to 300 mL
  3. washThis solution was washed in turn with 5% sodium carbonate solution, water, and brine
  4. concentrationconcentrated to an oil which
  5. customcrystallized
  6. dissolutionThis was dissolved in 25 mL of hot methanol which when
  7. temperaturecooled
  8. customgave crystals
  9. filtrationfiltered

Sources & evidence

ORD record
ord-3082afce19bc4b50a5b80e1168a7ec29
Source dataset
uspto-grants-1995_05
Patent number
US05418250

Reaction notes

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