Potassium Carbonate → HCID 19888656, compound

HRID 654194Notes

Reaction equation

HRID 654194 reaction equation
Cl.[CH3:2][NH:3][CH:4]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:13]([O-:15])=[O:14])[CH:10]=2)[CH2:5]1.Br[CH2:17][C:18]1[O:19][C:20]2[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][C:21]=2[CH:22]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[CH3:2][N:3]([CH:4]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:13]([O-:15])=[O:14])[CH:10]=2)[CH2:5]1)[CH2:17][C:18]1[O:19][C:20]2[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][C:21]=2[CH:22]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 114141792-(Bromomethyl)-5-nitro-1-benzofuran2×HCID 14835238HCID 14835238, compound

Product 1

HCID 19888656HCID 19888656, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Methylamino-5-nitroindane hydrochloride (0.28 g), 2-bromomethyl-5-nitrobenzofuran (0.31 g) and potassium carbonate (0.5 g) were stirred at room temperature in ethanol for 18 hours. A further portion of 2-bromomethyl-5-nitrobenzofuran (0.05 g) was then added and stirring was continued at room temperature for 5 hours. The solvent was evaporated in vacuo and the residue was dissolved in methylene chloride, washed with water, dried (MgSO4) and evaporated to give an oil which was purified by column chromatography on silica eluting with methylene chloride containing methanol (0% up to 1%). The product-containing fractions were combined and evaporated to give a gum which was triturated with diisopropyl ether and the precipitate was filtered off to give the title compound, yield 0.35 g, m.p. 109°-111°.

Workup

  1. customThe solvent was evaporated in vacuo
  2. dissolutionthe residue was dissolved in methylene chloride
  3. washwashed with water
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customto give an oil which
  7. customwas purified by column chromatography on silica eluting with methylene chloride
  8. additioncontaining methanol (0% up to 1%)
  9. customevaporated
  10. customto give a gum which
  11. customwas triturated with diisopropyl ether
  12. filtrationthe precipitate was filtered off

Sources & evidence

ORD record
ord-8725c518b7f04825b77b76ea3d2deb47
Source dataset
uspto-grants-1992_07
Patent number
US05130334

Reaction notes

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