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

HRID 1076897Notes

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]

Participants

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

temperatureUpon cooling
customthe solvent was evaporated
dissolutionthe remaining material was dissolved in heptane
filtrationfiltered
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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