Potassium Iodide → HCID 68136329, compound

HRID 1578636Notes

Reaction equation

HRID 1578636 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](=[C:12]([C:21](=[O:26])[CH2:22][CH2:23][CH2:24]Cl)[CH:13]=[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](=[C:12]([C:21](=[O:26])[CH2:22][CH2:23][CH2:24][N:31]([CH2:32][CH3:33])[CH2:29][CH3:30])[CH:13]=[CH:14][CH:15]=3)[CH2:10][C:9]=2[CH:8]=1)=[O:6])[CH3:30]

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 8021DiethylamineHCID 21559711HCID 21559711, compound

Product 1

HCID 68136329HCID 68136329, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 32.6 g (0.08 mole) of 2,8-bis(4-chlorobutyryl)thioxanthene, 2 g of potassium iodide, 100 ml of diethylamine and 100 ml of tetrahydrofuran is heated for 24 hours with stirring in a Paar bomb at 110°C. Upon cooling, the mixture is evaporated to near dryness. The residue is dissolved in methylene chloride, washed with water then with saturated NaCl solution, dried over magnesium sulfate and filtered. The filtrate is evaporated to near dryness and recrystallized several times from methanol-diethyl ether and from acetone-methanol to give 2,8-bis(4-diethylaminobutyryl)thioxanthene dihydrochloride. M.P. 188°-191°C.

Workup

  1. temperatureis heated for 24 hours
  2. temperatureUpon cooling
  3. customthe mixture is evaporated
  4. dissolutionThe residue is dissolved in methylene chloride
  5. washwashed with water
  6. dry with materialwith saturated NaCl solution, dried over magnesium sulfate
  7. filtrationfiltered
  8. customThe filtrate is evaporated
  9. customrecrystallized several times from methanol-diethyl ether

Sources & evidence

ORD record
ord-384c37697b094421b62236a3e6d33929
Source dataset
uspto-grants-1976_02
Patent number
US03937835

Reaction notes

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