Triethylamine → HCID 86644476, compound

HRID 2404544Notes

Reaction equation

HRID 2404544 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]1[C:19](CC(N)=O)=[CH:18][C:17]([O:24][CH2:25][C:26]([F:32])([F:31])[C:27]([F:30])([F:29])[F:28])=[N:16]1.[CH2:33]([N:35](CC)CC)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O>O1CCCC1>[C:33]([C:19]1[N:15]([C:3]2[CH:4]=[C:5]([S:9][CH2:10][C:11]([F:12])([F:13])[F:14])[C:6]([CH3:8])=[CH:7][C:2]=2[F:1])[N:16]=[C:17]([O:24][CH2:25][C:26]([F:31])([F:32])[C:27]([F:28])([F:30])[F:29])[CH:18]=1)#[N:35]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 131731766HCID 131731766, compound

Product 1

HCID 86644476HCID 86644476, compoundYield 80.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.80 g of 1-{2-fluoro-4-methyl-5-(2,2,2-trifluoroethylthio)phenyl}-3-(2,2,3,3,3-pentafluoropropoxy)pyrazole-5-carboxyamide was dissolved in 20 mL of tetrahydrofuran, 0.42 g of triethylamine was added, and 0.52 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 0.60 g of 5-cyano-1-{2-fluoro-4-methyl-5-(2,2,2-trifluoroethylthio)phenyl}-3-(2,2,3,3,3-pentafluoropropoxy)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-cdee1ce45e574bc29b11e741ae6591a7
Source dataset
uspto-grants-2014_08
Patent number
US08802713B2

Reaction notes

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