Iodine → HCID 20244553, compound

HRID 1164243Notes

Reaction equation

HRID 1164243 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:10](=[O:20])[C:11]=2[C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=[CH:5][CH:4]=1.[C:21]([CH2:29][C:30](=[O:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C1(=O)C=C1.II.[N:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1>>[C:30]([C:29]([C:21](=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[C:47]1[CH:48]=[C:49]2[N:44]([C:11]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)=[C:9]([C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=3)[C:10]2=[O:20])[CH:45]=[CH:46]1)(=[O:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

6

Reactant 5

HCID 807IodineHCID 1049Pyridine2×HCID 8433DibenzoylmethaneHCID 1377792-Cyclopropen-1-one2×HCID 122902702-Cyclopropen-1-one, 2,3-bis(4-methoxyphenyl)-

Product 1

HCID 20244553HCID 20244553, compoundYield 95%

Conditions

Temperature
90 °C

Procedure

A 10 percent solution of 2,3-di(4-methoxyphenyl) cyclopropenone in pyridine was refluxed under nitrogen for 15 minutes. The resulting solution was cooled slightly, and an equivalent amount of dibenzoylmethane based on the cyclopropenone was added to the green solution. The reaction mixture was refluxed for 60 minutes. The resulting reaction mixture was again cooled, and four equivalents of iodine dissolved in a small amount of pyridine was added to the reaction mixture. The mixture was further heated at 90° C. on a steam bath for 15 minutes. The bright blue solution was quenched by pouring it into cold excess dilute hydrochloric acid. The desired dye precipitated and was removed from the solution by filtering. A 95 percent yield of the desired dye was obtained based on the starting cyclopropenone. The dye was chromatographed on silica gel to provide a purified product. The maximum absorption of the dye was at 605 nm in chloroform solution. The structure of the dye was confirmed by mass spectroscopy, nuclear magnetic resonance and infrared analysis.

Workup

  1. temperatureThe resulting solution was cooled slightly
  2. additionwas added to the green solution
  3. temperatureThe reaction mixture was refluxed for 60 minutes
  4. customThe resulting reaction mixture
  5. temperaturewas again cooled
  6. additionwas added to the reaction mixture
  7. customThe bright blue solution was quenched
  8. additionby pouring it into cold excess dilute hydrochloric acid
  9. customThe desired dye precipitated
  10. customwas removed from the solution
  11. filtrationby filtering
  12. customA 95 percent yield of the desired dye was obtained
  13. customThe dye was chromatographed on silica gel
  14. customto provide a purified product
  15. customThe maximum absorption of the dye

Sources & evidence

ORD record
ord-d7faa597f7504881a58ee8588e312c94
Source dataset
uspto-grants-1983_01
Patent number
US04368247

Reaction notes

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