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

HRID 2249262Notes

Reaction equation

HRID 2249262 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 acetatem 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-611ad96b29d3444a86327667dd073279
Source dataset
uspto-grants-1991_08
Patent number
US05043454

Reaction notes

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