Potassium Carbonate → 3-(2-Azidoethyl)-7-nitro-1,2,4,5-tetrahydro-3H-3-benzazepine

HRID 329372ノート

反応式

HRID 329372 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 198720463-(2-Azidoethyl)-7-nitro-1,2,4,5-tetrahydro-3H-3-benzazepine

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-bcd262e619944d539617c53636939ca8
出典データセット
uspto-grants-1990_01
特許番号
US04891372

反応ノート

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