Potassium Iodide → HCID 86744666, compound

HRID 359481Notes

Reaction equation

HRID 359481 reaction equation
[OH:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][C:7]2[C:12]([C:13](=[O:19])[C:14]3[S:18][CH:17]=[CH:16][CH:15]=3)=[CH:11][CH:10]=[CH:9][N:8]=2)=[CH:4][CH:3]=1.[C:22](=[O:25])([O-:24])[O-].[K+].[K+].[I-].[K+].[CH3:30][N:31]([CH3:36])[CH2:32][CH2:33][CH2:34]Cl.C(OCC)(=[O:39])C>CN(C)C=O>[C:13]([OH:19])(=[O:39])/[CH:14]=[CH:15]/[C:22]([OH:24])=[O:25].[CH3:30][N:31]([CH3:36])[CH2:32][CH2:33][CH2:34][O:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C:7]2[C:12]([C:13](=[O:19])[C:14]3[S:18][CH:17]=[CH:16][CH:15]=3)=[CH:11][CH:10]=[CH:9][N:8]=2)=[CH:20][CH:21]=1

Participants

7

Reactant 5

HCID 4875Potassium IodideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 669603-Chloro-N,N-dimethyl-1-propanamineHCID 15135622HCID 15135622, compound

Product 1

HCID 86744666HCID 86744666, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 30 ml of dimethylformamide are added 3 g of 2-(4-hydroxyphenoxy)-3-(2-thenoyl)-pyridine, 1.7 g of potassium carbonate and 0.3 g of potassium iodide. The mixture is stirred at room temperature for 30 minutes. Thereto is added 1.5 g of 3-dimethylaminopropyl chloride, and the mixture is stirred at 50° C. for 4 hours. Thereafter, the reaction mixture is poured into ice-water, whereto ethyl acetate is added. The ethyl acetate is extracted with a dilute hydrochloric acid and the extract is rendered alkaline with potassium carbonate. The isolated oily substance is extracted with ethyl acetate. After the extract is washed with water and dried over anhydrous magnesium sulfate, the solvent is distilled off. The residue is converted into the salt with fumaric acid in ethanol. The salt is recrystallized from ethanol to give 2-[4-(3-dimethylaminopropoxy)phenoxy]-3-(2-thenoyl)pyridine fumarate 1/2 hydrate, m.p. 96°-99° C.

Workup

  1. stirringthe mixture is stirred at 50° C. for 4 hours
  2. additionis added
  3. extractionThe ethyl acetate is extracted with a dilute hydrochloric acid
  4. extractionThe isolated oily substance is extracted with ethyl acetate
  5. washAfter the extract is washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationthe solvent is distilled off
  8. customThe salt is recrystallized from ethanol

Sources & evidence

ORD record
ord-2828b7378b6042d1bc5998c87abaea69
Source dataset
uspto-grants-1991_03
Patent number
US05001137

Reaction notes

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