Potassium Iodide → 1,1'-(9H-Thioxanthene-2,7-diyl)bis[4-(diethylamino)butan-1-one]--hydrogen chloride (1/2)

HRID 1076894Notes

Reaction equation

[Cl:1][CH2:2][CH2:3][CH2:4][C:5]([C:7]1[CH:20]=[CH:19][C:18]2[S:17][C:16]3[C:11](=[CH:12][C:13]([C:21](=[O:26])[CH2:22][CH2:23][CH2:24]Cl)=[CH:14][CH:15]=3)[CH2:10][C:9]=2[CH:8]=1)=[O:6].[I-].[K+].[CH2:29]([NH:31][CH2:32][CH3:33])[CH3:30]>O1CCCC1>[ClH:1].[ClH:1].[CH2:29]([N:31]([CH2:32][CH3:33])[CH2:2][CH2:3][CH2:4][C:5]([C:7]1[CH:20]=[CH:19][C:18]2[S:17][C:16]3[C:11](=[CH:12][C:13]([C:21](=[O:26])[CH2:22][CH2:23][CH2:24][N:31]([CH2:32][CH3:33])[CH2:29][CH3:30])=[CH:14][CH:15]=3)[CH2:10][C:9]=2[CH:8]=1)=[O:6])[CH3:30]

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 32.6 g (0.08 mole) of 2,7-bis(4-chlorobutyryl)thioxanthene, 2 g of potassium iodide, 100 ml of diethylamine and 100 ml of tetrahydrofuran was heated for 24 hours with stirring in a Paar bomb at 110°C. Upon cooling the mixture was evaporated to near dryness. The residue was dissolved in methylene chloride, washed with water then with saturated NaCl solution, dried over magnesium sulfate and filtered. The filtrate was evaporated to near dryness and recrystallized several times from methanol-diethyl ether and from acetone-methanol to give the desired product. M.P. 188°-191°C.

Workup

temperaturewas heated for 24 hours
temperatureUpon cooling the mixture
customwas evaporated
dissolutionThe residue was dissolved in methylene chloride
washwashed with water
dry with materialwith saturated NaCl solution, dried over magnesium sulfate
filtrationfiltered
customThe filtrate was evaporated
customrecrystallized several times from methanol-diethyl ether

Sources & evidence

ORD record: ord-ff9402944aff491a8a73dbf5e8c9d32d
Source dataset: uspto-grants-1976_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03957988

Reaction notes

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