2-Iodoaniline → HCID 21753017, compound

HRID 1376767Notes

Reaction equation

HRID 1376767 reaction equation
[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]

Participants

4

Reactant 2

HCID 119952-IodoanilineHCID 10022190HCID 10022190, compound

Product 1

HCID 21753017HCID 21753017, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-e8144a8e40164f34a11e79a5cf5e66c3
Source dataset
uspto-grants-1997_09
Patent number
US05663336

Reaction notes

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