Imidazole → HCID 21704822, compound

HRID 1595824Notes

Reaction equation

HRID 1595824 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-])=O)=[CH:5][C:4]=1[Cl:12].[NH:13]1[CH:17]=[CH:16][N:15]=[CH:14]1>O1CCCC1>[Cl:12][C:4]1[CH:5]=[C:6]([NH2:9])[CH:7]=[CH:8][C:3]=1[CH2:2][N:13]1[CH:17]=[CH:16][N:15]=[CH:14]1

Participants

4

Reactant 2

HCID 795ImidazoleHCID 30163681-(Bromomethyl)-2-chloro-4-nitrobenzene

Product 1

HCID 21704822HCID 21704822, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 10 g of 4-bromomethyl-3-chloro nitrobenzene and 5.44 g of imidazole in 125 ml of tetrahydrofuran was refluxed for 4 hrs. The solvent was removed and the residue was dissolved in ethyl acetate. The solution was washed with water and dried over magnesium sulfate. The solvent was removed and the residue was extracted several times with ether. The ether extracts were diluted with two volumes of hexanes. 1-(2-Chloro-4-nitrobenzyl)-1H-imidazole (4.3 g) crystallized as a white solid. A 4 g portion of this material was mechanically stirred at reflux with 153 ml of methanol, 52 ml of water, 8.1 g of ammonium chloride, and 6.6 g of iron powder for 2 hrs. The hot mixture was filtered and solids were washed with hot methanol-tetrahydrofuran mixtures. Solvents were removed from the combined filtrates. The residue was extracted several times with hot ethyl acetate, The ethyl acetate solution was treat with magnesium sulfate and activated charcoal. Filtering and removing the solvent gave the 3.9 g of the title compound.

Workup

  1. customThe solvent was removed
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washThe solution was washed with water
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was removed
  6. extractionthe residue was extracted several times with ether
  7. additionThe ether extracts were diluted with two volumes of hexanes
  8. custom1-(2-Chloro-4-nitrobenzyl)-1H-imidazole (4.3 g) crystallized as a white solid
  9. temperatureat reflux with 153 ml of methanol, 52 ml of water, 8.1 g of ammonium chloride, and 6.6 g of iron powder for 2 hrs
  10. filtrationThe hot mixture was filtered
  11. washsolids were washed with hot methanol-tetrahydrofuran mixtures
  12. customSolvents were removed from the combined filtrates
  13. extractionThe residue was extracted several times with hot ethyl acetate
  14. additionThe ethyl acetate solution was treat with magnesium sulfate and activated charcoal
  15. filtrationFiltering
  16. customremoving the solvent

Sources & evidence

ORD record
ord-c14cf46614244688814e4b47351fa5d4
Source dataset
uspto-grants-2001_09
Patent number
US06288082B1

Reaction notes

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