Phosgene → HCID 86720673, compound

HRID 924614Notes

Reaction equation

HRID 924614 reaction equation
[Cl:1][C:2]1[C:3]([N:8]2[CH:12]=[CH:11][C:10](C(F)(F)F)=[N:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.C([Mg]Cl)(C)C.[C:22]([Cl:25])(Cl)=[O:23].[CH3:26][O:27]CCOC>O1CCCC1.C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:3]([N:8]2[C:12]([C:22]([Cl:25])=[O:23])=[CH:11][C:10]([O:27][CH3:26])=[N:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 6371PhosgeneHCID 80711,2-DimethoxyethaneHCID 179762913-chloro-2-(3-(trifluoromethyl)-1H-pyrazol-1-yl)pyridineHCID 178418918HCID 178418918, compound

Product 1

HCID 86720673HCID 86720673, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

In a reaction vessel equipped with a thermometer, septum, nitrogen inlet and stirring bar 1-(3-chloro-2-pyridyl)-3-trifloromethyl-1H-pyrazole (2.0 g, 0.01 mol) were dissolved in dry 1,2-dimethoxyethane (15 mL) and cooled to 0° C. By means of a syringe isopropyl magnesium chloride (11.4 mL of a 2 M solution in tetrahydrofuran) was added dropwise with stirring, while cooling the vessel with an ice bath and keeping the internal temperature below 5° C. After 3 h at this temperature a 20% (w/w) solution of phosgene in toluene (17 mL) were added dropwise with stirring. The mixture was allowed to warm to 23° C. and stirred for further 1 h at room temperature. The thus obtained reaction mixture was evaporated to dryness, redissolved in toluene and stirred for further 30 min. at 50° C. Solids were removed by filtration and washed with toluene. The combined filtrates were evaporated to dryness to yield 0.63 g of the title compound which was used in the next step without further purification.

Workup

  1. customIn a reaction vessel equipped with a thermometer, septum, nitrogen inlet
  2. temperaturewhile cooling the vessel with an ice bath
  3. customthe internal temperature below 5° C
  4. stirringwith stirring
  5. temperatureto warm to 23° C.
  6. stirringstirred for further 1 h at room temperature
  7. customThe thus obtained reaction mixture
  8. customwas evaporated to dryness
  9. dissolutionredissolved in toluene
  10. stirringstirred for further 30 min. at 50° C
  11. customSolids were removed by filtration
  12. washwashed with toluene
  13. customThe combined filtrates were evaporated to dryness

Sources & evidence

ORD record
ord-fdd6ae69979540aeb4ca0c9fcac51dbd
Source dataset
uspto-grants-2016_03
Patent number
US09282741B2

Reaction notes

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