Imidazole → HCID 20260911, compound

HRID 648054Notes

Reaction equation

HRID 648054 reaction equation
[Br:1][C:2]1[S:6][C:5]2[CH:7]=[C:8]([C:11](=[O:14])[CH2:12]Br)[CH:9]=[CH:10][C:4]=2[C:3]=1[CH3:15].[NH:16]1[CH:20]=[CH:19][N:18]=[CH:17]1.C(=O)([O-])[O-].[Na+].[Na+]>CC(C)=O>[Br:1][C:2]1[S:6][C:5]2[CH:7]=[C:8]([C:11](=[O:14])[CH2:12][N:16]3[CH:20]=[CH:19][N:18]=[CH:17]3)[CH:9]=[CH:10][C:4]=2[C:3]=1[CH3:15]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 10340Sodium CarbonateHCID 20260925HCID 20260925, compound

Product 1

HCID 20260911HCID 20260911, compoundYield 32.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2-bromo-6-bromoacetyl-3-methylbenzo[b]thiophene (1.74 g.), imidazole (0.34 g.) and sodium carbonate (1.50 g.) in acetone (20 ml.) was heated under reflux for 2 hours and then evaporated. Water (50 ml.) was added to the residue and the mixture was extracted several times with ethyl acetate. The combined extracts were dried (Na2SO4) and evaporated to give a solid which was chromatographed on silica gel. Elution with chloroform gave a solid which was crystallized from isopropanol/petrol (b.p. 60°-80°) to give 2-bromo-6-(1-imidazolyl)acetyl-3-methylbenzo[b]thiophene (0.55 g.), m.p. 184°-186° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. customevaporated
  4. additionWater (50 ml.) was added to the residue
  5. extractionthe mixture was extracted several times with ethyl acetate
  6. dry with materialThe combined extracts were dried (Na2SO4)
  7. customevaporated
  8. customto give a solid which
  9. customwas chromatographed on silica gel
  10. washElution with chloroform
  11. customgave a solid which
  12. customwas crystallized from isopropanol/petrol (b.p. 60°-80°)

Sources & evidence

ORD record
ord-d32aa8c458504ddfb4fbae3522b782e6
Source dataset
uspto-grants-1983_10
Patent number
US04410539

Reaction notes

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