Potassium Carbonate → 2-Ethoxy-5-[1-[4-(4-methylphenoxy)phenoxy]-ethyl]-1,3,4-thiadiazole

HRID 3782Notes

Reaction equation

HRID 3782 reaction equation
[CH3:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH:23]([C:25]1[S:26][C:27]([O:30][CH2:31][CH3:32])=[N:28][N:29]=1)[CH3:24]>CC(C)=O>[CH2:31]([O:30][C:27]1[S:26][C:25]([CH:23]([O:13][C:10]2[CH:11]=[CH:12][C:7]([O:6][C:5]3[CH:14]=[CH:15][C:2]([CH3:1])=[CH:3][CH:4]=3)=[CH:8][CH:9]=2)[CH3:24])=[N:29][N:28]=1)[CH3:32]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 6414404-(4-Methylphenoxy)phenolHCID 146523742-(1-Bromoethyl)-5-ethoxy-1,3,4-thiadiazole

Product 1

HCID 142309302-Ethoxy-5-[1-[4-(4-methylphenoxy)phenoxy]-ethyl]-1,3,4-thiadiazoleYield 73.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

0.84 g of 4-(4-methylphenoxy)phenol was dissolved in 5 ml of acetone followed by adding 0.87 g of anhydrous potassium carbonate and 1.0 g of 2-(1-bromoethyl)-5-ethoxy-1,3,4-thiadiazole. The resulting mixture was refluxed with stirring and heating for 2 hours. After cooling, insoluble salts were filtered off, and acetone was distilled off under reduced pressure. The residue was purified by chromatography on silica gel to obtain 1.1 g of the compound No. 10 described in Table 1.

Workup

  1. temperatureThe resulting mixture was refluxed
  2. temperatureheating for 2 hours
  3. temperatureAfter cooling
  4. filtrationinsoluble salts were filtered off
  5. distillationacetone was distilled off under reduced pressure
  6. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-08f23e697a564844a42b9eee52f2f3d1
Source dataset
uspto-grants-1988_02
Patent number
US04722934

Reaction notes

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