Iodine → HCID 12985516, compound

HRID 1270429Notes

Reaction equation

HRID 1270429 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH:3]=[C:2]1[C:11]1[C:15](=[O:16])[N:14]([CH3:17])[C:13](=[O:18])[C:12]=1[C:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:21]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH:20]=1.II>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH3:17][N:14]1[C:13](=[O:18])[C:12]2[C:19]3[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[N:21]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C:20]=3[C:3]3[O:4][C:5]4[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=4[O:1][C:2]=3[C:11]=2[C:15]1=[O:16]

Participants

5

Reactant 2

HCID 807IodineHCID 18449807HCID 18449807, compound

Product 1

HCID 12985516HCID 12985516, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

218.1 μmol of the compound obtained in Step A above and 5.91 mmol of double-sublimed iodine are dissolved in 500 ml of toluene inside the cell of an irradiation apparatus. After irradiating for 30 minutes, with stirring, the reaction mixture is cooled and then diluted with ethyl acetate. Washing with 80 ml of 20% aqueous sodium thiosulphate solution is carried out until the organic phase is decolourised. The aqueous phase is extracted with ethyl acetate three times, and then the organic phases are combined and directly concentrated in vacuo. A brown, semi-oily, semi-solid residue is collected. The procedure is repeated a further five times in the same manner, using the same amounts. The crude reaction products of the six procedures are combined. Washing with ethyl acetate is carried out on the six crude reaction products, which are then filtered. The filtrate is evaporated and then taken up in methanol, filtered, rinsed with methanol and then dried in vacuo, allowing the expected product to be isolated.

Workup

  1. customAfter irradiating for 30 minutes
  2. temperaturethe reaction mixture is cooled
  3. washWashing with 80 ml of 20% aqueous sodium thiosulphate solution
  4. extractionThe aqueous phase is extracted with ethyl acetate three times
  5. concentrationdirectly concentrated in vacuo
  6. customA brown, semi-oily, semi-solid residue is collected
  7. customThe crude reaction products of the six procedures
  8. washWashing with ethyl acetate
  9. customreaction products, which
  10. filtrationare then filtered
  11. customThe filtrate is evaporated
  12. filtrationfiltered
  13. washrinsed with methanol
  14. customdried in vacuo
  15. customto be isolated

Sources & evidence

ORD record
ord-d2b76f38fc7d46e8b8d026299c252e8c
Source dataset
uspto-grants-2007_04
Patent number
US07202255B2

Reaction notes

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