HCID 86644461, compound → HCID 86644460, compound

HRID 2404532Notes

Reaction equation

HRID 2404532 reaction equation
[C:1]([NH:4][C:5]1[N:9]([C:10]2[CH:15]=[C:14]([S:16](C)=O)[C:13]([CH3:19])=[CH:12][C:11]=2[F:20])[N:8]=[C:7]([O:21][CH2:22][C:23]([F:29])([F:28])[C:24]([F:27])([F:26])[F:25])[CH:6]=1)(=[O:3])[CH3:2]>C(OC(=O)C)(=O)C>[C:1]([NH:4][C:5]1[N:9]([C:10]2[CH:15]=[C:14]([SH:16])[C:13]([CH3:19])=[CH:12][C:11]=2[F:20])[N:8]=[C:7]([O:21][CH2:22][C:23]([F:29])([F:28])[C:24]([F:27])([F:26])[F:25])[CH:6]=1)(=[O:3])[CH3:2]

Participants

3

Reactant 1

HCID 86644461HCID 86644461, compound

Product 1

HCID 86644460HCID 86644460, compoundYield 90.6%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
120 °C

Procedure

Then, 4.5 g of 5-acetylamino-1-(2-fluoro-4-methyl-5-methylsulfinylphenyl)-3-(2,2,3,3,3-pentafluoropropoxy)pyrazole was dissolved in 200 mL of acetic anhydride, followed by stirring at 120° C. for 6 hours. Acetic anhydride was distilled off under reduced pressure, the obtained residue was dissolved in 150 mL of ethanol, and 4.0 g of potassium carbonate was added, followed by stirring at room temperature for 12hours. Neutralization with a 6N hydrochloric acid aqueous solution was carried out, 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 silica gel column chromatography (developing solvent ethyl acetate:hexane=1:4) to obtain 3.8 g of 5-acetylamino-1-(2-fluoro-4-methyl-5-mercaptophenyl)-3-(2,2,3,3,3-pentafluoropropoxy)pyrazole (1H-NMR (CDCL3/TMS δ (ppm) value) δ: 2.09 (3H, s), 2.38 (3H, s), 3.39 (1H, s), 4.66 (2H, t), 6.20 (1H, s), 7.09 (1H, d), 7.14 (1H, brs), 7.39 (1H, d)).

Workup

  1. distillationAcetic anhydride was distilled off under reduced pressure
  2. dissolutionthe obtained residue was dissolved in 150 mL of ethanol
  3. addition4.0 g of potassium carbonate was added
  4. stirringby stirring at room temperature for 12hours
  5. extractionextraction with ethyl acetate
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customthe obtained residue was purified by silica gel column chromatography (developing solvent ethyl acetate:hexane=1:4)

Sources & evidence

ORD record
ord-e45a0dfc72d14edd9ac05449bf8a810c
Source dataset
uspto-grants-2014_08
Patent number
US08802713B2

Reaction notes

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