Methanol → Methyl 1-(2,4-dibromophenyl)-2-methylimidazole-4-carboxylate

HRID 247774Notes

Reaction equation

HRID 247774 reaction equation
C[O-].[Na+].[CH3:4][C:5]1[NH:6][CH:7]=[C:8]([C:10]([O:12][CH3:13])=[O:11])[N:9]=1.CO.F[C:17]1[CH:22]=[CH:21][C:20]([Br:23])=[CH:19][C:18]=1[Br:24]>CN(C)C=O.O>[Br:23][C:20]1[CH:19]=[C:18]([Br:24])[CH:17]=[CH:22][C:21]=1[N:6]1[CH:7]=[C:8]([C:10]([O:12][CH3:13])=[O:11])[N:9]=[C:5]1[CH3:4]

Participants

7

Reactant 4

HCID 887MethanolHCID 150342,4-Dibromo-1-fluorobenzeneHCID 10942334Sodium MethoxideHCID 178498881HCID 178498881, compound

Product 1

HCID 14882422Methyl 1-(2,4-dibromophenyl)-2-methylimidazole-4-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

14.1 g of 30% strength sodium methylate solution was added to 10.9 g (0.078 mol) of methyl 2-methylimidazole-4-carboxylate in 100 ml of dimethylformamide; the methanol which formed was removed completely. 38.1 g (0.15 mol) of 1-fluoro-2,4-dibromobenzene was added to the dimethylformamide solution remaining, and the mixture was refluxed for 2 hours. Water was then added, extraction carried out with ethyl acetate and the ethyl acetate phase was washed with water. After removal of the solvent from the organic phase, there was obtained a residue which crystallized on trituration with diisopropyl ether.

Workup

  1. customwas removed completely
  2. temperaturethe mixture was refluxed for 2 hours
  3. extractionextraction
  4. washthe ethyl acetate phase was washed with water
  5. customAfter removal of the solvent from the organic phase
  6. customthere was obtained a residue which
  7. customcrystallized on trituration with diisopropyl ether

Sources & evidence

ORD record
ord-c248daf6efcc4c929c5910c3cdedcb9c
Source dataset
uspto-grants-1993_05
Patent number
US05207820

Reaction notes

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