Imidazole → HCID 14581296, compound

HRID 1382189Notes

Reaction equation

HRID 1382189 reaction equation
[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10](=[O:18])[C:11]1[CH:16]=[CH:15][C:14](F)=[CH:13][CH:12]=1.[H-].[Na+].[NH:22]1[CH:26]=[CH:25][N:24]=[CH:23]1>CN(C=O)C>[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10](=[O:18])[C:11]1[CH:16]=[CH:15][C:14]([N:22]2[CH:26]=[CH:25][N:24]=[CH:23]2)=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 24758Sodium hydrideHCID 13306905HCID 13306905, compound

Product 1

HCID 14581296HCID 14581296, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
120 °C

Procedure

A solution of methyl-2-(4-fluorobenzoyl)benzoate (5.31 g, 21 mmol) in 23 mL of DMF is added dropwise to a solution of NaH (0.91 g, 23 mmol) and imidazole (1.43 g, 21 mmol) in 35 mL of DMF. The resulting mixture is heated at 120° C. for 20 hours under N2. After cooling, the product is poured onto ice and extracted with CHCl3 (4×30 mL). The combined extracts are dried (Na2SO4) and evaporated to give crude product. Chromatographic purification of the crude residue on silica gel (using EtOAc as the eluent) gives pure methyl-2-[4(1H-imidazol-1-yl)benzoyl]benzoate. M.P. 134.5°-136.5° C.

Workup

  1. temperatureAfter cooling
  2. additionthe product is poured onto ice
  3. extractionextracted with CHCl3 (4×30 mL)
  4. dry with materialThe combined extracts are dried (Na2SO4)
  5. customevaporated
  6. customto give crude product
  7. customChromatographic purification of the crude residue on silica gel (

Sources & evidence

ORD record
ord-3d701769bf384deaac194e3098f14b62
Source dataset
uspto-grants-1989_02
Patent number
US04806535

Reaction notes

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