Imidazole → HCID 70456035, compound

HRID 280594Notes

Reaction equation

HRID 280594 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:15]=[CH:14][C:8]2[S:9][C:10]([CH2:12]Br)=[CH:11][C:7]=2[CH:6]=1)=[O:4].[NH:16]1[CH:20]=[CH:19][N:18]=[CH:17]1.C(=O)(O)[O-].[Na+]>CC(C)=O>[CH3:1][O:2][C:3]([C:5]1[CH:15]=[CH:14][C:8]2[S:9][C:10]([CH2:12][C:17]3[NH:16][CH:20]=[CH:19][N:18]=3)=[CH:11][C:7]=2[CH:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 516892Sodium BicarbonateHCID 13663066HCID 13663066, compound

Product 1

HCID 70456035HCID 70456035, compoundYield 49.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2-bromomethylbenzo[b]thiophene-5-carboxylic acid methyl ester (1.71 g), imidazole (4.08 g) and sodium bicarbonate (0.55 g) in acetone (50 ml) was heated under reflux for 3 hours and then evaporated. The residue was partitioned between ethyl acetate and water. The organic layer was washed with water, dried (Na2SO4) and evaporated to give a solid which was chromatographed on silica gel. Elution with chloroform gave first a small amount of starting material followed by product. Evaporation of the product containing fractions gave a solid which was crystallised from ethyl acetate/petrol (b.p. 60°-80°) to give 2-(1-imidazolylmethyl)benzo[b]thiophene-5-carboxylic acid methyl ester (0.81 g), m.p. 127°-128°.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hours
  3. customevaporated
  4. customThe residue was partitioned between ethyl acetate and water
  5. washThe organic layer was washed with water
  6. dry with materialdried (Na2SO4)
  7. customevaporated
  8. customto give a solid which
  9. customwas chromatographed on silica gel
  10. washElution with chloroform
  11. customgave first a small amount of starting material
  12. customEvaporation of the product
  13. additioncontaining fractions
  14. customgave a solid which
  15. customwas crystallised from ethyl acetate/petrol (b.p. 60°-80°)

Sources & evidence

ORD record
ord-7c6e03c4e9794beda9d7594f21e6dbcf
Source dataset
uspto-grants-1986_05
Patent number
US04590200

Reaction notes

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