Imidazole → HCID 70457205, compound

HRID 280586Notes

Reaction equation

HRID 280586 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][N:5]=[CH:4]1.[CH2:8]([O:10][C:11]([C:13]1[CH:24]=[CH:23][C:16]2[S:17][C:18]([CH2:21]Cl)=[C:19]([CH3:20])[C:15]=2[CH:14]=1)=[O:12])[CH3:9]>CN(C)C=O>[CH2:8]([O:10][C:11]([C:13]1[CH:24]=[CH:23][C:16]2[S:17][C:18]([CH2:21][C:4]3[NH:3][CH:7]=[CH:6][N:5]=3)=[C:19]([CH3:20])[C:15]=2[CH:14]=1)=[O:12])[CH3:9]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 24758Sodium hydrideHCID 13663054HCID 13663054, compound

Product 1

HCID 70457205HCID 70457205, compoundYield 46.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Sodium hydride (0.5 g of 50% dispersion in mineral oil) was added portionwise to a stirred solution of imidazole (0.68 g) in dry N,N-dimethylformamide (DMF) (30 ml) and the mixture was stirred at room temperature for 30 minutes. A solution of 2-chloromethyl-3-methylbenzo[b]thiophene-5-carboxylic acid ethyl ester (2.70 g) in dry N,N-dimethylformamide (5 ml) was added, the mixture was stirred for 2 hours and then evaporated. The residue was dissolved in ethyl acetate and the solution was washed well with water and dried (Na2SO4). Evaporation of the solvent gave an oil which was chromatographed on silica gel. Elution with chloroform/petrol (b.p. 40°-60° C.) (3:1) first gave some impurity followed by pure product. Evaporation of the product containing fractions gave a solid which was crystallized from ethyl acetate/petrol (b.p. 60°-80° C.) to give 2-(1-imidazolylmethyl)-3-methylbenzo[b]thiophene-5-carboxylic acid ethyl ester (1.40 g), m.p. 126°-127° C.

Workup

  1. stirringthe mixture was stirred for 2 hours
  2. customevaporated
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washthe solution was washed well with water
  5. dry with materialdried (Na2SO4)
  6. customEvaporation of the solvent
  7. customgave an oil which
  8. customwas chromatographed on silica gel
  9. washElution with chloroform/petrol (b.p. 40°-60° C.) (3:1)
  10. customfirst gave some impurity
  11. customEvaporation of the product
  12. additioncontaining fractions
  13. customgave a solid which
  14. customwas crystallized from ethyl acetate/petrol (b.p. 60°-80° C.)

Sources & evidence

ORD record
ord-f7b42fb175104b2fbe26aef51d21086a
Source dataset
uspto-grants-1986_05
Patent number
US04590200

Reaction notes

Loading…