2-Iodoaniline → HCID 21753017、化合物

HRID 1376767ノート

反応式

HRID 1376767 の反応式
[CH3:1][O:2][C:3]([C:5]1[CH2:10][C:9](O[Si](C)(C)C)=[C:8](O[Si](C)(C)C)[CH2:7][C:6]=1[C:21]([O:23][CH3:24])=[O:22])=[O:4].[I:25][C:26]1[CH:32]=[CH:31][CH:30]=[CH:29][C:27]=1[NH2:28]>C(O)(=O)C>[CH3:1][O:2][C:3](=[O:4])[C:5]1[C:6](=[CH:7][C:8]([NH:28][C:27]2[CH:29]=[CH:30][CH:31]=[CH:32][C:26]=2[I:25])=[C:9]([NH:28][C:27]2[CH:29]=[CH:30][CH:31]=[CH:32][C:26]=2[I:25])[CH:10]=1)[C:21]([O:23][CH3:24])=[O:22]

参加物

4

反応物 2

HCID 119952-IodoanilineHCID 100221904,5-Bis(trimethylsilyloxy)cyclohexa-1,4-diene-1,2-dicarboxylic acid dimethyl ester

生成物 1

HCID 21753017HCID 21753017、化合物

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

A solution of 2.4 g (6 mmol) of 4,5-bis(trimethylsilyloxy)cyclohexa- 1,4-diene- 1,2-dicarboxylic acid dimethyl ester (Example 1a) and 5.3 g (24 mmol) of 2-iodoaniline in 24 ml of glacial acetic acid ii boiled under reflux for 2 hours. The reaction mixture is cooled, the solvent is evaporated off and the dark-brown residue is dissolved in dichloromethane and the solution is washed in succession with 20 ml of 1N HCl, 50 ml of saturated NaHCO3 and twice with 20 ml of water, dried with sodium sulfate and concentrated by evaporation. The residue obtained after concentration by evaporation is chromatographed on silica gel with ethyl acetate/hexane 2:1 and the product fractions are concentrated by evaporation, yielding the title compound in the form of a yellow foam: 1H-NMR (DMSO-d6): δ=7.91 (dxd, J1 =8, J2 =1, 2H) 7.39 (d×d×d, J1 =10, J2 =8, J3 =1, 2H), 7.32 (br s, 2H), 7.22-7.05 (m, 2H), 7.01 (s, 2H), 6.88 (t×d, Jt =8, Jd =1, 2H), 3.73 (s,6H).

後処理

  1. temperatureunder reflux for 2 hours
  2. temperatureThe reaction mixture is cooled
  3. customthe solvent is evaporated off
  4. dissolutionthe dark-brown residue is dissolved in dichloromethane
  5. washthe solution is washed in succession with 20 ml of 1N HCl, 50 ml of saturated NaHCO3 and twice with 20 ml of water
  6. dry with materialdried with sodium sulfate
  7. concentrationconcentrated by evaporation
  8. customThe residue obtained
  9. concentrationafter concentration
  10. customby evaporation
  11. customis chromatographed on silica gel with ethyl acetate/hexane 2:1
  12. concentrationthe product fractions are concentrated by evaporation

出典と根拠

ORDレコード
ord-e8144a8e40164f34a11e79a5cf5e66c3
出典データセット
uspto-grants-1997_09
特許番号
US05663336

反応ノート

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