18-Crown-6 → HCID 18689507, compound

HRID 1871868Notes

Reaction equation

HRID 1871868 reaction equation
Cl[C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5]([Cl:12])=[C:4]([O:13][CH2:14][C:15]#[CH:16])[N:3]=1.C1OCCOCCOCCOCCOCCOC1.[F-:35].[K+].S1(CCCC1)(=O)=O>C(OC)(C)(C)C>[Cl:12][C:5]1[C:4]([O:13][CH2:14][C:15]#[CH:16])=[N:3][C:2]([F:35])=[C:7]([C:8]([F:11])([F:10])[F:9])[CH:6]=1

Participants

6

Reactant 4

HCID 2855718-Crown-6HCID 31347SulfolaneHCID 522689Potassium FluorideHCID 18689506HCID 18689506, compound

Product 1

HCID 18689507HCID 18689507, compound

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
152.5 °C

Procedure

47.3 g (0.175 mol) of 2,5-dichloro-6-propargyloxy-3-trifluoromethylpyridine, 0.5 g (1.89 mmol) of 18-crown-6 and 15.2 g (0.263 mol) of potassium fluoride were added to 150 ml of sulfolane and it was stirred at 150-155° C. for 5 hours. After cooling, the reaction mixture was stirred with methyl tert-butyl ether and separated off from the inorganic precipitate. The filtrate was extracted four times with water, dried and concentrated. The residue was filtered with suction with methylene chloride through a suction filter containing silica gel and concentrated, 31.4 g (71% of theory) of the title compound of n24D =1.4732 being obtained.

Workup

  1. temperatureAfter cooling
  2. customseparated off from the inorganic precipitate
  3. extractionThe filtrate was extracted four times with water
  4. customdried
  5. concentrationconcentrated
  6. filtrationThe residue was filtered with suction with methylene chloride through a suction
  7. filtrationfilter
  8. additioncontaining silica gel
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-6583b03e5599430b8c5decb62ad679dd
Source dataset
uspto-grants-2000_08
Patent number
US06107253

Reaction notes

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