Potassium Iodide → HCID 515415, compound

HRID 1076899Notes

Reaction equation

HRID 1076899 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][C:6]([C:8]1[CH:21]=[CH:20][C:19]2[S:18][C:17]3[C:12](=[CH:13][C:14]([C:22](=[O:28])[CH2:23][CH2:24][CH2:25][CH2:26]Cl)=[CH:15][CH:16]=3)[CH2:11][C:10]=2[CH:9]=1)=[O:7].[I-].[K+].[CH2:31]([NH:34][CH2:35][CH:36]=[CH2:37])[CH:32]=[CH2:33]>O1CCCC1>[CH2:31]([N:34]([CH2:35][CH:36]=[CH2:37])[CH2:2][CH2:3][CH2:4][CH2:5][C:6]([C:8]1[CH:21]=[CH:20][C:19]2[S:18][C:17]3[C:12](=[CH:13][C:14]([C:22](=[O:28])[CH2:23][CH2:24][CH2:25][CH2:26][N:34]([CH2:35][CH:36]=[CH2:37])[CH2:31][CH:32]=[CH2:33])=[CH:15][CH:16]=3)[CH2:11][C:10]=2[CH:9]=1)=[O:7])[CH:32]=[CH2:33]

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 31279DiallylamineHCID 12340289HCID 12340289, compound

Product 1

HCID 515415HCID 515415, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 22.3 g (0.05 mole) of 2,7-bis(5-chlorovaleryl)thioxanthene, 1 g of potassium iodide, 100 ml of diallylamine and 200 ml of tetrahydrofuran was placed in a Paar bomb and heated to 120°C. with stirring for 24 hours. Upon cooling, the mixture was filtered and the filtrate evaporated to dryness. The resulting residue was dissolved in dilute HCl and extracted with ether. The aqueous portion was made basic, extracted with methylene chloride, dried over magnesium sulfate and filtered. The filtrate was heated to boiling, treated with charcoal, filtered and filtrate evaporated to dryness. The residue was chromatographed on a column of alumina and eluted with methylene chloride. The resulting oil was dissolved in diethyl ether, dried over molecular sieves, filtered and the ether evaporated. This process was repeated several times to yield the desired product.

Workup

  1. temperatureUpon cooling
  2. filtrationthe mixture was filtered
  3. customthe filtrate evaporated to dryness
  4. dissolutionThe resulting residue was dissolved in dilute HCl
  5. extractionextracted with ether
  6. extractionextracted with methylene chloride
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. temperatureThe filtrate was heated to boiling
  10. additiontreated with charcoal
  11. filtrationfiltered
  12. customfiltrate evaporated to dryness
  13. customThe residue was chromatographed on a column of alumina
  14. washeluted with methylene chloride
  15. dissolutionThe resulting oil was dissolved in diethyl ether
  16. customdried over molecular sieves
  17. filtrationfiltered
  18. customthe ether evaporated

Sources & evidence

ORD record
ord-b8e6f1b2b81c45ac8a1a2eaabd73bec5
Source dataset
uspto-grants-1976_05
Patent number
US03957988

Reaction notes

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