Sodium Iodide → HCID 19813447, compound

HRID 467093Notes

Reaction equation

HRID 467093 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1.Br[CH2:15][C:16]1[O:17][C:18]2[CH:24]=[C:23]([N+:25]([O-:27])=[O:26])[CH:22]=[CH:21][C:19]=2C=1.[I-].[Na+].C(=O)([O-])[O-].[K+].[K+].C(#[N:38])C>>[CH3:1][N:2]([CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1)[CH2:15][C:16]1[O:17][C:18]2[CH:24]=[C:23]([N+:25]([O-:27])=[O:26])[CH:22]=[CH:21][C:19]=2[N:38]=1

Participants

6

Reactant 5

HCID 5238Sodium IodideHCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 2794239N-methyl-4-nitrophenethylamineHCID 18521725HCID 18521725, compound

Product 1

HCID 19813447HCID 19813447, compound

Procedure

N-Methyl-4-nitrophenethylamine (0.84 g, 4.7 mmole), 2-bromomethyl-6-nitrobenzofuran (1.2 g, 4.7 mmole), sodium iodide (0.7 g, 4.7 mmole) and potassium carbonate (0.71 g, 5.2 mmole) were heated in acetonitrile at the reflux temperature for 18 hours. The cooled reaction mixture was then filtered and the filtrate evaporated to dryness and purified by chromatography on silica eluting with methylene chloride/hexane (1:1) followed by methylene chloride/methanol (19:1). The product-containing fractions were combined and evaporated and the residue was treated with decolourising charcoal in ethanol to afford an oil which solidified on standing. Recrystallisation of the solid from ethanol/methylene chloride gave the title compound, yield 0.27 g, m.p. 69°-69.5°.

Workup

  1. customThe cooled reaction mixture
  2. filtrationwas then filtered
  3. customthe filtrate evaporated to dryness
  4. custompurified by chromatography on silica eluting with methylene chloride/hexane (1:1)
  5. customevaporated
  6. additionthe residue was treated with decolourising charcoal in ethanol
  7. customto afford an oil which
  8. customRecrystallisation of the solid from ethanol/methylene chloride

Sources & evidence

ORD record
ord-65488b4350dd41d98b4b1d567a3368df
Source dataset
uspto-grants-1992_10
Patent number
US05158964

Reaction notes

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