Potassium Carbonate → 7-Nitro-3-(5-nitrobenzofur-2-ylmethyl)-1,2,4,5-tetrahydro-3H-3-benzazepine

HRID 620733Notes

Reaction equation

HRID 620733 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].Br[CH2:16][C:17]1[O:18][C:19]2[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][C:20]=2[CH:21]=1.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]([CH2:16][C:17]3[O:18][C:19]4[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][C:20]=4[CH:21]=3)[CH2:11][CH2:12][C:6]=2[CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 113100427-Nitro-2,3,4,5-tetrahydro-1H-benzo[D]azepineHCID 114141792-(Bromomethyl)-5-nitro-1-benzofuran

Product 1

HCID 212450557-Nitro-3-(5-nitrobenzofur-2-ylmethyl)-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-bromomethyl-5-nitrobenzofuran (0.93 g) and potassium carbonate (0.5 g) in acetonitrile were heated under reflux for 8 hours. After cooling the solvent was removed in vacuo, the residue dissolved in methylene chloride and washed three times with aqueous sodium carbonate and three times with brine. The organic layer was dried (Na2SO4) and evaporated in vacuo to give an oil methylene chloride. The product-containing fractions were combined and evaporated in vacuo to give an oil which was triturated with hexane and the evaporated in vacuo to give the title compound as a foam, yield 0.76 g.

Workup

  1. temperatureunder reflux for 8 hours
  2. temperatureAfter cooling the solvent
  3. customwas removed in vacuo
  4. dissolutionthe residue dissolved in methylene chloride
  5. washwashed three times with aqueous sodium carbonate and three times with brine
  6. dry with materialThe organic layer was dried (Na2SO4)
  7. customevaporated in vacuo
  8. customto give an oil methylene chloride
  9. customevaporated in vacuo
  10. customto give an oil which
  11. customwas triturated with hexane
  12. customthe evaporated in vacuo

Sources & evidence

ORD record
ord-6f79a58eb4ea41dda8e1c558b39a4123
Source dataset
uspto-grants-1989_04
Patent number
US04822793

Reaction notes

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