Acetone → HCID 21221551, compound

HRID 1584602Notes

Reaction equation

HRID 1584602 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:11][C:10]3[CH2:12][CH2:13][CH:14]([NH2:16])[CH2:15][C:9]=3[C:8]=2[CH:17]=1)([O-:3])=[O:2].I[CH2:19][CH3:20].C(=O)([O-])[O-].[K+].[K+].[CH3:27][C:28](C)=O>>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:11][C:10]3[CH2:12][CH2:13][CH:14]([N:16]([CH2:19][CH3:20])[CH2:27][CH3:28])[CH2:15][C:9]=3[C:8]=2[CH:17]=1)([O-:3])=[O:2]

Participants

5

Reactant 4

HCID 180AcetoneHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 21221615HCID 21221615, compound

Product 1

HCID 21221551HCID 21221551, compoundYield 45%

Procedure

A mixture of 0.88 gm (3.79 mMol) 8-nitro-1,2,3,4-tetrahydro-2-dibenzofuranamine, 0.89 gm (5.68 mMol) iodoethane and 1.58 gm (11.4 mMol) potassium carbonate in 50 mL acetone was heated at reflux for 3 hours. The reaction mixture was concentrated under reduced pressure and the residue dissolved in water. This mixture was extracted well with chloroform. The organic phases were combined, dried over potassium carbonate and concentrated under reduced pressure. The residue was subjected to radial chromatography (silica gel, 2 mm). Fractions containing product were combined and concentrated under reduced pressure to provide 0.49 gm (45%) 8-nitro-1,2,3,4-tetrahydro-2-diethylaminodibenzofuran as a yellow oil.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. dissolutionthe residue dissolved in water
  5. extractionThis mixture was extracted well with chloroform
  6. dry with materialdried over potassium carbonate
  7. concentrationconcentrated under reduced pressure
  8. additionFractions containing product
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3a334cc0a608457686946ffc4bb853fe
Source dataset
uspto-grants-1999_08
Patent number
US05932739

Reaction notes

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