N-bromobutanimide → HCID 86644428, compound

HRID 2404506Notes

Reaction equation

HRID 2404506 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][CH2:22][C:23]([F:29])([F:28])[C:24]([F:27])([F:26])[F:25])[CH:3]=1.[Br:30]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:16])([F:17])[F:18])[C:10]([CH3:19])=[CH:9][C:8]=2[F:20])[N:5]=[C:4]([O:21][CH2:22][C:23]([F:28])([F:29])[C:24]([F:25])([F:27])[F:26])[C:3]=1[Br:30]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 86644427HCID 86644427, compound

Product 1

HCID 86644428HCID 86644428, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2.0 g of 5-amino-1-{2-fluoro-4-methyl-5-(2,2,2-trifluoroethylthio)phenyl}-3-(2,2,3,3,3-pentafluoropropoxy)pyrazole was dissolved in 50 mL of acetonitrile, and 0.8g of N-bromosuccinimide was added under cooling with ice. After stirring for 10minutes 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 2.0 g of 5-amino-4-bromo 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. 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-3161f190ffdb41e3a2f139ede373943c
Source dataset
uspto-grants-2014_08
Patent number
US08802713B2

Reaction notes

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