Imidazole → HCID 54002689, compound

HRID 1637187Notes

Reaction equation

HRID 1637187 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[H-].[Na+].Br[CH2:9][C:10]1[CH:11]=[CH:12][C:13]2[C:17]([Cl:18])=[C:16]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[S:15][C:14]=2[CH:24]=1>CN(C)C=O>[Cl:18][C:17]1[C:13]2[CH:12]=[CH:11][C:10]([CH2:9][N:1]3[CH:5]=[CH:4][N:3]=[CH:2]3)=[CH:24][C:14]=2[S:15][C:16]=1[C:19]([O:21][CH2:22][CH3:23])=[O:20]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 24758Sodium hydrideHCID 19347979HCID 19347979, compound

Product 1

HCID 54002689HCID 54002689, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Imidazole (2.0 g, 30 mmol) was added in portions to a stirred suspension of sodium hydride (0.48 g of 60% dispersion in mineral oil, 12 mmol) in anhydrous dimethylformamide (15 ml) at 0° C., under a nitrogen atmosphere. After 40 minutes, ethyl 6-bromomethyl-3-chlorobenzo[b]thiophene-2-carboxylate (Preparation 10, 3.33 g, 10 mmol) was added. After 2 hours the mixture was partitioned between ethyl acetate and water. The organic layer was separated and washed with more water, dried (magnesium sulfate), and evaporated under reduced pressure. The residue was flash chromatographed on silica gel using 5% methanol in dichloromethane as eluant, and the isolated product was crystallised from diethyl ether to give the title compound as a colourless solid (2.02 g).

Workup

  1. customAfter 2 hours the mixture was partitioned between ethyl acetate and water
  2. customThe organic layer was separated
  3. washwashed with more water
  4. dry with materialdried (magnesium sulfate)
  5. customevaporated under reduced pressure
  6. customchromatographed on silica gel using 5% methanol in dichloromethane as eluant
  7. customthe isolated product was crystallised from diethyl ether

Sources & evidence

ORD record
ord-c4fb5b65665b4ee3bd5a66d2f416dfdd
Source dataset
uspto-grants-2000_03
Patent number
US06040309

Reaction notes

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