Imidazole → HCID 70479575, compound

HRID 648029Notes

Reaction equation

HRID 648029 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[H-].[Na+].[CH3:8][O:9][C:10]([C:12]1[S:16][C:15]2[CH:17]=[CH:18][C:19]([CH2:21]Cl)=[CH:20][C:14]=2[C:13]=1[CH3:23])=[O:11]>CN(C)C=O>[CH3:8][O:9][C:10]([C:12]1[S:16][C:15]2[CH:17]=[CH:18][C:19]([CH2:21][C:2]3[NH:1][CH:5]=[CH:4][N:3]=3)=[CH:20][C:14]=2[C:13]=1[CH3:23])=[O:11]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 24758Sodium hydrideHCID 13662991HCID 13662991, compound

Product 1

HCID 70479575HCID 70479575, compoundYield 32.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of imidazole (0.23 g.) in dry N,N-dimethylformamide (10 ml.) was added sodium hydride (0.17 g. of 50% dispersion in mineral oil) and the mixture was stirred for 30 minutes. A solution of 5-chloromethyl-3-methylbenzo[b]thiophene-2-carboxylic acid methyl ester (0.82 g.) in dry N,N-dimethylformamide (10 ml.) was then added dropwise with stirring and the resulting mixture was stirred at room temperature for 2.5 hours and then evaporated. The residue was poured into water and the mixture was extracted several times with ethyl acetate. The combined extracts were washed with water, dried (Na2SO4) and evaporated to give a solid which was chromatographed on silica gel. Elution with chloroform gave first some impurity followed by pure product. The product containing fractions were combined to give a solid which was crystallized from ethyl acetate/petrol (b.p. 60°-80°) to give 5-(1-imidazolylmethyl)-3-methylbenzo[b]thiophene-2-carboxylic acid methyl ester (0.30 g.), m.p. 136°-138°.

Workup

  1. stirringwith stirring
  2. stirringthe resulting mixture was stirred at room temperature for 2.5 hours
  3. customevaporated
  4. additionThe residue was poured into water
  5. extractionthe mixture was extracted several times with ethyl acetate
  6. washThe combined extracts were washed with water
  7. dry with materialdried (Na2SO4)
  8. customevaporated
  9. customto give a solid which
  10. customwas chromatographed on silica gel
  11. washElution with chloroform
  12. customgave first some impurity
  13. additionThe product containing fractions
  14. customto give a solid which
  15. customwas crystallized from ethyl acetate/petrol (b.p. 60°-80°)

Sources & evidence

ORD record
ord-b9d8703754014faea270f95681d3a555
Source dataset
uspto-grants-1983_10
Patent number
US04410539

Reaction notes

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