Sodium Iodide → 7-Nitro-3-(2-[4-nitrophenoxy]ethyl)-1,2,4,5-tetrahydro-3H-3-benzazepine

HRID 329368Notes

Reaction equation

HRID 329368 reaction equation
[N+:1]([C:4]1[CH:14]=[CH:13][C:7]2[CH2:8][CH2:9][NH:10][CH2:11][CH2:12][C:6]=2[CH:5]=1)([O-:3])=[O:2].[N+:15]([C:18]1[CH:27]=[CH:26][C:21]([O:22][CH2:23][CH2:24]Cl)=[CH:20][CH:19]=1)([O-:17])=[O:16].[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[N+:1]([C:4]1[CH:14]=[CH:13][C:7]2[CH2:8][CH2:9][N:10]([CH2:24][CH2:23][O:22][C:21]3[CH:20]=[CH:19][C:18]([N+:15]([O-:17])=[O:16])=[CH:27][CH:26]=3)[CH2:11][CH2:12][C:6]=2[CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 27645871-(2-Chloroethoxy)-4-nitrobenzeneHCID 113100427-Nitro-2,3,4,5-tetrahydro-1H-benzo[D]azepine

Product 1

HCID 198720567-Nitro-3-(2-[4-nitrophenoxy]ethyl)-1,2,4,5-tetrahydro-3H-3-benzazepine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

7-Nitro-1,2,4,5-tetrahydro-3H-3-benzazepine (0.7 g), 2-[4-nitrophenoxy]ethyl chloride (0.73 g) (see C. A. [1955], 49, 3163e), sodium iodide (0.5 g) and potassium carbonate in acetonitrile (50 ml) were heated under reflux for 3 days. After cooling, the solvent was removed in vacuo, the residue dissolved in ethyl acetate and washed once with water, once with sodium carbonate and twice with brine. The organic layer was dried (Na2SO4) and evaporated in vacuo 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 in vacuo to give the product as an orange oil, yield 1.0 g.

Workup

  1. temperatureunder reflux for 3 days
  2. temperatureAfter cooling
  3. customthe solvent was removed in vacuo
  4. dissolutionthe residue dissolved in ethyl acetate
  5. washwashed once with water, once with sodium carbonate and twice with brine
  6. dry with materialThe organic layer was dried (Na2SO4)
  7. customevaporated in vacuo
  8. customto give an oil which
  9. customwas purified by column chromatography on silica eluting with methylene chloride
  10. additioncontaining methanol (0% up to 1%)
  11. customevaporated in vacuo

Sources & evidence

ORD record
ord-df6e885d74794028bc52d4a90935e264
Source dataset
uspto-grants-1990_01
Patent number
US04891372

Reaction notes

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