Dimethylformamide → HCID 15987432, compound

HRID 260062Notes

Reaction equation

HRID 260062 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][S:22][CH2:23][CH2:24]Cl.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>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][S:22][CH3:21])[N:14]=2)=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 109652-Chloroethyl methyl sulfideHCID 11430Potassium CarbonateHCID 15285934HCID 15285934, compound

Product 1

HCID 15987432HCID 15987432, compoundYield 67.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

2 g of 5-[4-(4,4,4-trifluorobutoxy)phenyl]-1,3,4-oxadiazol-2(3H)-one, 1.14 g of 2-chloroethyl methyl sulphide, 2.4 g of potassium carbonate and 30 ml of dimethylformamide are introduced into a 50 ml three-necked round-bottomed flask. The reaction mixture is heated to 90° C. and is maintained at this temperature overnight, then poured into water. The precipitate formed is collected by filtration, washed with water and taken up in ethyl acetate. The solution is dried over sodium sulphate and the solvent is then evaporated off. After recrystallization in diisopropyl ether, 1.7 g of product are obtained.

Workup

  1. temperatureis maintained at this temperature overnight
  2. customThe precipitate formed
  3. filtrationis collected by filtration
  4. washwashed with water
  5. dry with materialThe solution is dried over sodium sulphate
  6. customthe solvent is then evaporated off
  7. customAfter recrystallization in diisopropyl ether

Sources & evidence

ORD record
ord-a34b860802df4802b4d81636ebf018ff
Source dataset
uspto-grants-1996_06
Patent number
US05525619

Reaction notes

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