Potassium Iodide → HCID 515415, compound

HRID 1578638Notes

Reaction equation

HRID 1578638 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 is placed in a Paar bomb and heated to 120°C with stirring for 24 hours. Upon cooling, the mixture is filtered and the filtrate evaporated to dryness. The resulting residue is dissolved in dilute HCl and extracted with ether. The aqueous portion is made basic, extracted with methylene chloride, dried over magnesium sulfate and filtered. The filtrate is heated to boiling, treated with charcoal, filtered and filtrate evaporated to dryness. The residue is chromatographed on a column of alumina and eluted with methylene chloride. The resulting oil is dissolved in diethyl ether, dried over molecular sieves, filtered and the ether evaporated. This process is repeated several times to yield 2,7-bis(5-diallylaminovaleryl)thioxanthene.

Workup

  1. temperatureUpon cooling
  2. filtrationthe mixture is filtered
  3. customthe filtrate evaporated to dryness
  4. dissolutionThe resulting residue is 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 is heated to boiling
  10. additiontreated with charcoal
  11. filtrationfiltered
  12. customfiltrate evaporated to dryness
  13. customThe residue is chromatographed on a column of alumina
  14. washeluted with methylene chloride
  15. dissolutionThe resulting oil is dissolved in diethyl ether
  16. customdried over molecular sieves
  17. filtrationfiltered
  18. customthe ether evaporated

Sources & evidence

ORD record
ord-c58162d67f9143d5a9fef2f6cf765fe5
Source dataset
uspto-grants-1976_02
Patent number
US03937835

Reaction notes

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