Potassium Carbonate → HCID 19872046, compound

HRID 329372Notes

Reaction equation

HRID 329372 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].CS(O[CH2:20][CH2:21][N:22]=[N+:23]=[N-:24])(=O)=O.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[N:22]([CH2:21][CH2:20][N:10]1[CH2:9][CH2:8][C:7]2[CH:13]=[CH:14][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][C:6]=2[CH2:12][CH2:11]1)=[N+:23]=[N-:24]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 112751972-Azidoethyl methanesulfonateHCID 113100427-Nitro-2,3,4,5-tetrahydro-1H-benzo[D]azepine

Product 1

HCID 19872046HCID 19872046, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

7-Nitro-1,2,4,5-tetrahydro-3H-3-benzazepine (1.1 g), 2-methanesulphonyloxyethyl azide (0.92 g) and potassium carbonate (0.76 g) were heated under reflux in acetonitrile for 18 hours. The solvent was evaporated in vacuo and the residue taken up in ethyl acetate then washed three times with aqueous sodium carbonate and three times with brine. The organic layer was dried, filtered and evaporated in vacuo to give an oil which was purified by chromatography on silica eluting with ethyl acetate/hexane (1:1). The product-containing fractions were combined and evaporated to give the title compound as an oil, yield 0.65 g, which was used without further purification.

Workup

  1. customThe solvent was evaporated in vacuo
  2. washthen washed three times with aqueous sodium carbonate and three times with brine
  3. customThe organic layer was dried
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customto give an oil which
  7. customwas purified by chromatography on silica eluting with ethyl acetate/hexane (1:1)
  8. customevaporated

Sources & evidence

ORD record
ord-bcd262e619944d539617c53636939ca8
Source dataset
uspto-grants-1990_01
Patent number
US04891372

Reaction notes

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