Triethylamine → HCID 86644485, compound

HRID 2404551Notes

Reaction equation

HRID 2404551 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([S:9][CH2:10][C:11]([F:14])([F:13])[F:12])=[CH:4][C:3]=1[N:15]1C(=NO)C(=C)[C:17]([O:23][C:24]([F:33])([F:32])[CH:25]([F:31])[O:26][C:27]([F:30])([F:29])[F:28])=[N:16]1.C([N:36]([CH2:39][CH3:40])CC)C.F[C:42](F)(F)C(OC(=O)C(F)(F)F)=O>O1CCCC1>[C:39]([C:40]1[N:15]([C:3]2[CH:4]=[C:5]([S:9][CH2:10][C:11]([F:14])([F:12])[F:13])[C:6]([CH3:8])=[CH:7][C:2]=2[F:1])[N:16]=[C:17]([O:23][C:24]([F:32])([F:33])[CH:25]([F:31])[O:26][C:27]([F:28])([F:29])[F:30])[CH:42]=1)#[N:36]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 86644484HCID 86644484, compound

Product 1

HCID 86644485HCID 86644485, compoundYield 103.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Then, 0.28 g of 1-{2-fluoro-4-methyl-5-(2,2,2-trifluoroethylthio)phenyl}-5-(hydroxyimino)methylene-3-{1,1,2-trifluoro-2-(trifluoromethoxy)ethoxy}pyrazole was dissolved in 10 mL of tetrahydrofuran, 0.12 g of triethylamine was added, and 0.13 g of trifluoroacetic anhydride was slowly dropwise added under cooling with ice. After stirring at room temperature for 2 hours, the solvent was distilled off under reduced pressure, and extraction with ethyl acetate was carried out. The organic layer was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and the obtained residue was purified by column chromatography (developing solvent ethyl acetate:hexane=1:4) to obtain 0.28 g of 5-cyano-1-{2-fluoro-4-methyl-5-(2,2,2-trifluoroethylthio)phenyl}-3-{1,1,2-trifluoro-2-(trifluoromethoxy)ethoxy}pyrazole.

Workup

  1. temperatureunder cooling with ice
  2. distillationthe solvent was distilled off under reduced pressure, and extraction with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customthe obtained residue was purified by column chromatography (developing solvent ethyl acetate:hexane=1:4)

Sources & evidence

ORD record
ord-c6d5c4cf571c490aa536b12fdf7ba0b9
Source dataset
uspto-grants-2014_08
Patent number
US08802713B2

Reaction notes

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