N-bromobutanimide → HCID 10160605, compound

HRID 861246Notes

Reaction equation

HRID 861246 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([C:19]([F:22])([F:21])[F:20])[CH:3]=1.[Br:23]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[NH2:1][C:2]1[N:6]([C:7]2[C:8]([Cl:18])=[CH:9][C:10]([C:14]([F:15])([F:16])[F:17])=[CH:11][C:12]=2[Cl:13])[N:5]=[C:4]([C:19]([F:22])([F:21])[F:20])[C:3]=1[Br:23]

Participants

4

Reactant 2

HCID 67184N-bromobutanimide2×HCID 22618376HCID 22618376, compound

Product 1

HCID 10160605HCID 10160605, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-trifluoromethylpyrazole (3.64 g) and N-bromosuccinimide (1.78 g) in carbon tetrachloride (30 ml ) was stirred and heated under reflux for 1 hour. Further N-bromosuccinimide (0.89 g) was added, and reflux was continued for a further 1 hour. The mixture was cooled, filtered, and the filtrate was evaporated in vacuo to give an orange solid. Recrystallization from petroleum ether gave 5-amino-4-bromo-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-trifluoromethylpyrazole in the form of white crystals (2.6 g) m.p. 119°-120° C.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 1 hour
  3. temperaturereflux
  4. temperatureThe mixture was cooled
  5. filtrationfiltered
  6. customthe filtrate was evaporated in vacuo
  7. customto give an orange solid
  8. customRecrystallization from petroleum ether

Sources & evidence

ORD record
ord-c9f89fa7c9954777b72f4993e3de31d4
Source dataset
uspto-grants-1998_02
Patent number
US05714191

Reaction notes

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