Chlorosuccinimide → HCID 86644467, compound

HRID 2404536Notes

Reaction equation

HRID 2404536 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[C:11]([S:13][CH2:14][C:15]([F:18])([F:17])[F:16])[C:10]([CH3:19])=[CH:9][C:8]=2[F:20])[N:5]=[C:4]([O:21][C:22]([F:30])([F:29])[CH:23]([F:28])[C:24]([F:27])([F:26])[F:25])[CH:3]=1.[Cl:31]N1C(=O)CCC1=O>C(#N)C>[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[C:11]([S:13][CH2:14][C:15]([F:17])([F:18])[F:16])[C:10]([CH3:19])=[CH:9][C:8]=2[F:20])[N:5]=[C:4]([O:21][C:22]([F:29])([F:30])[CH:23]([F:28])[C:24]([F:25])([F:26])[F:27])[C:3]=1[Cl:31]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 86644424HCID 86644424, compound

Product 1

HCID 86644467HCID 86644467, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2.9 g of 5-amino-1-{2-fluoro-4-methyl-5-(2,2,2-trifluoroethylthio)phenyl}-3-(1,1,2,3,3,3-hexafluoropropoxy)pyrazole was dissolved in 30 mL of acetonitrile, and 0.9g of N-chlorosuccinimide was added under cooling with ice. After stirring for 30minutes under cooling with ice, the solvent was distilled off under reduced pressure, extraction with ethyl acetate was carried out, and the organic layer was dried over anhydrous magnesium sulfate. Then, 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 3.12 g of 5-amino-4-chloro-1-{2-fluoro-4-methyl-5-(2,2,2-trifluoroethylthio)phenyl}-3-(1,1,2,3,3,3-hexafluoropropoxy)pyrazole.

Workup

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

Sources & evidence

ORD record
ord-f29036f141cd4a2b91f798709eaf091f
Source dataset
uspto-grants-2014_08
Patent number
US08802713B2

Reaction notes

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