Potassium Iodide → HCID 20065115, compound

HRID 359479Notes

Reaction equation

HRID 359479 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]([CH3:39])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]Cl.C(OCC)(=[O:42])C>CN(C)C=O>[C:13]([OH:19])(=[O:42])/[CH:14]=[CH:15]/[C:22]([OH:24])=[O:25].[CH3:30][N:31]([CH3:39])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][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 129470316-Chloro-N,N-dimethylhexan-1-amineHCID 15135622HCID 15135622, compound

Product 1

HCID 20065115HCID 20065115, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 50 ml of dimethylformamide are added 5 g of 2-(4-hydroxyphenoxy)-3-(2-thenoyl)pyridine, 3.5 g of potassium carbonate and 0.5 g of potassium iodide, and the mixture is stirred at room temperature for 30 minutes. Thereto is added 4.1 g of 6-dimethylaminohexyl chloride. The mixture is stirred at 50° C. for 7 hours. Then, the mixture is poured into ice-water, followed by addition of ethyl acetate thereto. The ethyl acetate layer is extracted with hydrochloric acid and the extract is rendered alkaline with potassium carbonate. The isolated oily substance is extracted with ethyl acetate. The extract is washed with water and dried over anhydrous magnesium sulfate. Thereafter, 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-(6-dimethylaminohexyloxy)phenoxy]-3-(2-thenoyl)pyridine fumarate, m.p. 98°-101° C.

Workup

  1. stirringThe mixture is stirred at 50° C. for 7 hours
  2. extractionThe ethyl acetate layer is extracted with hydrochloric acid
  3. extractionThe isolated oily substance is extracted with ethyl acetate
  4. washThe extract is washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThereafter, the solvent is distilled off
  7. customThe salt is recrystallized from ethanol

Sources & evidence

ORD record
ord-3d1bf7a46be94701880eea4359e25db0
Source dataset
uspto-grants-1991_03
Patent number
US05001137

Reaction notes

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