18-Crown-6 → HCID 15452060, compound

HRID 1005487Notes

Reaction equation

HRID 1005487 reaction equation
Cl[C:2]1[C:9]([Cl:10])=[CH:8][CH:7]=[C:6]([C:11]([F:14])([F:13])[F:12])[C:3]=1[C:4]#[N:5].[F-:15].[K+].C1OCCOCCOCCOCCOCCOC1>CN(C)C=O>[Cl:10][C:9]1[C:2]([F:15])=[C:3]([C:6]([C:11]([F:14])([F:13])[F:12])=[CH:7][CH:8]=1)[C:4]#[N:5]

Participants

5

Reactant 3

HCID 2855718-Crown-6HCID 522689Potassium FluorideHCID 109775462,3-Dichloro-6-(trifluoromethyl)benzonitrile

Product 1

HCID 15452060HCID 15452060, compoundYield 72.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 0.96 g of 2,3-dichloro-6-trifluoromethylbenzonitrile in 7 ml of N,N-dimethylformamide was added 0.46 g of spray-dried potassium fluoride and 0.1 g of 18-crown-6-ether and the mixture was stirred for 6 hours at 100° C. under a nitrogen atmosphere. After cooling, the reaction mixture was poured into ice water and extracted with ethyl acetate. The organic layer was washed with saturated saline solution and dried over anhydrous magnesium sulfate. After distilling the solvent under reduced pressure, the crude product obtained was purified by using silica gel column chromatography to obtain 0.65 g of the title compound(mp. 43-44° C.).

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated saline solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationAfter distilling the solvent under reduced pressure
  6. customthe crude product obtained
  7. customwas purified

Sources & evidence

ORD record
ord-9cbea0cc61ff4c699ec7bf5d529e5133
Source dataset
uspto-grants-2000_04
Patent number
US06054605

Reaction notes

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