18-Crown-6 → HCID 178474078, compound

HRID 2069842Notes

Reaction equation

HRID 2069842 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:11])[CH3:10])=[N:6][CH:7]=1.Cl[C:13](C(O[Na])=O)([F:15])[F:14].C1OCCOCCOCCOCCOCCOC1>CC#N>[Br:1][C:2]1[CH:3]=[CH:4]/[C:5](=[N:8]\[C:9](=[O:11])[CH3:10])/[N:6]([CH:13]([F:15])[F:14])[CH:7]=1

Participants

5

Reactant 3

HCID 2855718-Crown-6HCID 2930972-Acetamido-5-bromopyridineHCID 178526069HCID 178526069, compound

Product 1

HCID 178474078HCID 178474078, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of N-(5-Bromo-pyridin-2-yl)-acetamide (1 g, 4.6 mmol) in 30 ml CH3CN was added ClCF2COONa (848 mg, 5.58 mmol), followed by 18-Crown-6 (244 mg, 0.93 mmol). The reaction mixture was heated to reflux for 12 hrs. Then the reaction mixture was cooled down and the solvent was removed under reduced pressure. To this was added methylene dichloride and washed with water. Organic layer was dried over anhy sodium sulphate and concentrated under reduced pressure to furnish the crude N-[5-Bromo-1-difluoromethyl-1H-pyridin-(2E)-ylidene]-acetamide. This was carried to the next step without purification.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 12 hrs
  3. temperatureThen the reaction mixture was cooled down
  4. customthe solvent was removed under reduced pressure
  5. additionTo this was added methylene dichloride
  6. washwashed with water
  7. dry with materialOrganic layer was dried over anhy sodium sulphate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f9669db8d33a49abb28b5a4b62e88b27
Source dataset
uspto-grants-2012_10
Patent number
US08299077B2

Reaction notes

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