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Potassium Iodide → 1-Pentanone, 1,1'-(9H-thioxanthene-2,7-diyl)bis(5-(diethylamino)-, dihydrochloride

HRID 1076897
Notes
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Reaction equation

HRID 1076897 reaction equation
[Cl:1][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:33][CH2:34][CH3:35])[CH3:32]>O1CCCC1>[ClH:1].[ClH:1].[CH2:31]([N:33]([CH2:34][CH3:35])[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:33]([CH2:34][CH3:35])[CH2:31][CH3:32])=[CH:15][CH:16]=3)[CH2:11][C:10]=2[CH:9]=1)=[O:7])[CH3:32]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 8021DiethylamineHCID 12340289HCID 12340289, compound

Product 1

HCID 2168601-Pentanone, 1,1'-(9H-thioxanthene-2,7-diyl)bis(5-(diethylamino)-, dihydrochloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
106 °C

Procedure

A mixture of 20 g (0.0046 mole) of 2,7-bis(5-chlorovaleryl)-thioxanthene, 2 g of potassium iodide, 150 ml of diethylamine and 250 ml of tetrahyrofuran was heated to 106°C. in a Paar bomb for 24 hours with stirring. Upon cooling, the solvent was evaporated, and the remaining material was dissolved in heptane and filtered. The solution was acidified with ethereal HCl and the resulting precipitate was recrystallized several times from methanol and ethyl acetate to give the desired product. M.P. 197.5°-199.5°C.

Workup

  1. temperatureUpon cooling
  2. customthe solvent was evaporated
  3. dissolutionthe remaining material was dissolved in heptane
  4. filtrationfiltered
  5. customthe resulting precipitate was recrystallized several times from methanol and ethyl acetate

Sources & evidence

ORD record
ord-1e53ffb71f4848ac9e83860db440e307
Source dataset
uspto-grants-1976_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US03957988

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes