Dimethylformamide → HCID 19080746, compound

HRID 963147Notes

Reaction equation

HRID 963147 reaction equation
CN(C)[CH:3]=[O:4].P(Cl)(Cl)([Cl:8])=O.[CH2:11]([N:13]1[C:17](O)=[CH:16][C:15]([C:19]([F:22])([F:21])[F:20])=[N:14]1)[CH3:12]>>[Cl:8][C:17]1[N:13]([CH2:11][CH3:12])[N:14]=[C:15]([C:19]([F:22])([F:21])[F:20])[C:16]=1[CH:3]=[O:4]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 178463141HCID 178463141, compound

Product 1

HCID 19080746HCID 19080746, compound

Procedure

Dimethylformamide (13.36 g 182.7 mmol) was cooled to about 0° C. and 60.69 g (395.8 mmol) of phosphoryl chloride was added dropwise with stirring to form a pink slurry. This was allowed to warm to ambient temperature and then 32.92 g (182.7 mmol) of 1-ethyl-5-hydroxy-3-(trifluoromethyl)pyrazole was added dropwise with stirring to it. There appeared to be an endotherm and the mixture became dark brown to black. The mixture was then heated at reflux (108° C.) overnight and, after cooling, was poured into an ice-water mixture with stirring. A precipitate formed and then dissolved. The solution was extracted with dichloromethane (3×150 mL) and the combined extracts were dried over magnesium sulfate, filtered, and concentrated under reduced pressure to obtain the title compound as a dark brown to black oil.

Workup

  1. customto form a pink slurry
  2. stirringwith stirring to it
  3. temperatureThe mixture was then heated
  4. temperatureat reflux (108° C.) overnight
  5. temperatureafter cooling
  6. stirringwith stirring
  7. customA precipitate formed
  8. dissolutiondissolved
  9. extractionThe solution was extracted with dichloromethane (3×150 mL)
  10. dry with materialthe combined extracts were dried over magnesium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a793bdb28b8b472295db511c05d8d1ff
Source dataset
uspto-grants-1998_06
Patent number
US05763359

Reaction notes

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