Imidazole → HCID 56989060, compound

HRID 648023Notes

Reaction equation

HRID 648023 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][N:5]=[CH:4]1.[CH3:8][O:9][C:10]([C:12]1[S:16][C:15]2[CH:17]=[CH:18][C:19]([CH2:21]Br)=[CH:20][C:14]=2[CH:13]=1)=[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:4]3[NH:3][CH:7]=[CH:6][N:5]=3)=[CH:20][C:14]=2[CH:13]=1)=[O:11]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 24758Sodium hydrideHCID 13662981HCID 13662981, compound

Product 1

HCID 56989060HCID 56989060, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

NaH (0.34 g.:50% dispersion in oil) was added portion-wise to a stirred solution of imidazole (0.48 g.) in dry dimethylformamide (DMF) (20 ml.). After 1/2 hour a solution of 5-bromomethylbenzo[b]thiophene-2-carboxylic acid methyl ester (2.0 g.) in DMF (15 ml.) was added dropwise. After stirring at room temperature for 1 hour, the solvent was removed under reduced pressure and H2O (100 ml.) added to the residue. The aqueous solution was then extracted with EtOAc (3×50 ml.) and the combined organic extracts were washed (H2O), dried (MgSO4), filtered and evaporated to give a solid which was recrystallized from MeOH/H2O to give 5-(1-imidazolylmethyl)benzo[b]thiophene-2-carboxylic acid methyl ester, 0.7 g., m.p. 168°-169° C.

Workup

  1. customthe solvent was removed under reduced pressure and H2O (100 ml.)
  2. additionadded to the residue
  3. extractionThe aqueous solution was then extracted with EtOAc (3×50 ml.)
  4. washthe combined organic extracts were washed (H2O)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customto give a solid which
  9. customwas recrystallized from MeOH/H2O

Sources & evidence

ORD record
ord-3dbbe1334dda459283bc321adf895ec3
Source dataset
uspto-grants-1983_10
Patent number
US04410539

Reaction notes

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