Potassium Iodide → 2-{4-[1-(5-Ethoxy-1,3,4-thiadiazol-2-yl)ethoxy]phenoxy}pyridine

HRID 2352546Notes

Reaction equation

HRID 2352546 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[O:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Br[CH:24]([C:26]1[S:27][C:28]([O:31][CH2:32][CH3:33])=[N:29][N:30]=1)[CH3:25]>O.CN(C)C=O>[CH2:32]([O:31][C:28]1[S:27][C:26]([CH:24]([O:14][C:11]2[CH:12]=[CH:13][C:8]([O:7][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)=[CH:9][CH:10]=2)[CH3:25])=[N:30][N:29]=1)[CH3:33]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 146523734-(Pyridin-2-yloxy)phenolHCID 146523742-(1-Bromoethyl)-5-ethoxy-1,3,4-thiadiazole

Product 1

HCID 146523752-{4-[1-(5-Ethoxy-1,3,4-thiadiazol-2-yl)ethoxy]phenoxy}pyridineYield 61.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 4-(2-pyridyloxy)phenol (0.75 g), anhydrous potassium carbonate (0.67 g), potassium iodide (0.07 g), cupuric oxide (0.02 g) and 7 ml of dimethyl formamide, was added 2-(1-bromoethyl)-5-ethoxy-1,3,4-thiadiazole (0.95 g) under stirring, and further stirred at 80° C. for one hour. After cooling and pouring water, the resulting solution was extracted with ethyl acetate, washed with water and then dried over anhydrous magnesium sulfate. Ethyl acetate was distilled off under a reduced pressure and the residue was purified on column chromatography to obtain 0.84 g of the compound (No. 1) described in Table 1.

Workup

  1. stirringfurther stirred at 80° C. for one hour
  2. temperatureAfter cooling
  3. extractionthe resulting solution was extracted with ethyl acetate
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationEthyl acetate was distilled off under a reduced pressure
  7. customthe residue was purified on column chromatography

Sources & evidence

ORD record
ord-49d62c41a0254fb58028d0fcd3f714e1
Source dataset
uspto-grants-1989_10
Patent number
US04877804

Reaction notes

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