Water → HCID 9884600, compound

HRID 260059Notes

Reaction equation

HRID 260059 reaction equation
[F:1][C:2]([F:20])([F:19])[CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[O:17][C:16](=[O:18])[NH:15][N:14]=2)=[CH:9][CH:8]=1.[CH3:21][O:22][CH2:23][CH2:24]Cl.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[F:20][C:2]([F:1])([F:19])[CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[O:17][C:16](=[O:18])[N:15]([CH2:24][CH2:23][O:22][CH3:21])[N:14]=2)=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 123162-Chloroethyl methyl etherHCID 15285934HCID 15285934, compound

Product 1

HCID 9884600HCID 9884600, compoundYield 83.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

1.8 g of 5-[4-(4,4,4-trifluorobutoxy)phenyl]-1,3,4-oxadiazol-2(3H)-one, 0.77 g of 2-chloroethyl methyl ether and a solution of 2.15 g of potassium carbonate in 20 ml of dimethylformamide are introduced into a 25 ml three-necked flask. The mixture is heated to 100° C. for 1 h 45 min and is then cooled and poured into 100 ml of water. The precipitate formed is drained, washed with 3 times 50 ml of water and then dissolved in ethyl acetate. The solution is dried over sodium sulphate and filtered, and the solvent is evaporated off. 1.8 g of product are obtained, which product is recrystallized in 10 ml of 96 % ethanol. 1.5 g of product are finally obtained.

Workup

  1. temperatureis then cooled
  2. customThe precipitate formed
  3. washwashed with 3 times 50 ml of water
  4. dissolutiondissolved in ethyl acetate
  5. dry with materialThe solution is dried over sodium sulphate
  6. filtrationfiltered
  7. customthe solvent is evaporated off

Sources & evidence

ORD record
ord-26aad2d44f964bbbadb2ce31fb0a3ddd
Source dataset
uspto-grants-1996_06
Patent number
US05525619

Reaction notes

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