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

HRID 1076894
Notes
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Reaction equation

HRID 1076894 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 8021DiethylamineHCID 12340288HCID 12340288, compound

Product 1

HCID 123402921,1'-(9H-Thioxanthene-2,7-diyl)bis[4-(diethylamino)butan-1-one]--hydrogen chloride (1/2)

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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

  1. temperaturewas heated for 24 hours
  2. temperatureUpon cooling the mixture
  3. customwas evaporated
  4. dissolutionThe residue was dissolved in methylene chloride
  5. washwashed with water
  6. dry with materialwith saturated NaCl solution, dried over magnesium sulfate
  7. filtrationfiltered
  8. customThe filtrate was evaporated
  9. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes