Potassium Carbonate → HCID 10058013, compound

HRID 1613727Notes

Reaction equation

HRID 1613727 reaction equation
Br[C:2]1[CH:3]=[C:4]([O:8]C)[CH:5]=[CH:6][CH:7]=1.[CH3:10][C:11]1[NH:12][CH:13]=[CH:14][N:15]=1.C(=O)([O-])[O-].[K+].[K+]>CN1CCCC1=O>[CH3:10][C:11]1[N:12]([C:2]2[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=2)[CH:13]=[CH:14][N:15]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 127492-MethylimidazoleHCID 169713-Bromoanisole

Product 1

HCID 10058013HCID 10058013, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A stirred mixture of 3-bromoanisole (100 g, 0.53 mole), 2-methylimidazole (41 g, 0.50 mole), potassium carbonate (96 g, 0.60 mole), cuprous chloride (2.5 g) and N-methyl-2-pyrrolidinone (300 ml) was heated at reflux temperature for 15 hr and then concentrated to remove the solvent and excess 3-bromoanisole. The residue was partitioned between ethyl acetate and water. The ethyl acetate layer was concentrated to a black syrup that was then dissolved in toluene and extracted twice with water and then extracted with 48% hydrobromic acid solution. The hydrobomic acid extract was heated at reflux temperature for 7 hr and then distilltion of water and methylbromide was begun with addition of additional 48% hydrobromic acid solution as necessary to maintain a reasonable volume. Distillation was continued until the distillation head temperature reached 124° C. The mixture was concentrated under vacuum. The concentrate was diluted with 500 ml of water and basified to pH 8 with addition of potassium carbonate in small portions. The precipitate was collected, washed with water, and dried to give 39.7 g. Recrystallization from 50% aqueous ethanol gave 31.4 g (36%), mp 178°-181° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 15 hr
  3. concentrationconcentrated
  4. customto remove the solvent and excess 3-bromoanisole
  5. customThe residue was partitioned between ethyl acetate and water
  6. concentrationThe ethyl acetate layer was concentrated to a black syrup that
  7. dissolutionwas then dissolved in toluene
  8. extractionextracted twice with water
  9. extractionextracted with 48% hydrobromic acid solution
  10. extractionThe hydrobomic acid extract
  11. temperaturewas heated
  12. temperatureat reflux temperature for 7 hr
  13. additiondistilltion of water and methylbromide was begun with addition of additional 48% hydrobromic acid solution as necessary
  14. temperatureto maintain a reasonable volume
  15. distillationDistillation
  16. customreached 124° C
  17. concentrationThe mixture was concentrated under vacuum
  18. additionThe concentrate was diluted with 500 ml of water and basified to pH 8 with addition of potassium carbonate in small portions
  19. customThe precipitate was collected
  20. washwashed with water
  21. customdried
  22. customto give 39.7 g
  23. customRecrystallization from 50% aqueous ethanol
  24. customgave 31.4 g (36%), mp 178°-181° C.

Sources & evidence

ORD record
ord-dd5fec88935847538f1e87300df8a16d
Source dataset
uspto-grants-1993_03
Patent number
US05194446

Reaction notes

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