N-bromobutanimide → HCID 21188072, compound

HRID 1383598Notes

Reaction equation

HRID 1383598 reaction equation
[Cl: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]#[N:20])[C:3]=1[C:21]#[CH:22].[Br:23]N1C(=O)CCC1=O>CC(C)=O.[N+]([O-])([O-])=O.[Ag+]>[Br:23][C:22]#[C:21][C:3]1[C:4]([C:19]#[N:20])=[N:5][N:6]([C:7]2[C:8]([Cl:18])=[CH:9][C:10]([C:14]([F:15])([F:17])[F:16])=[CH:11][C:12]=2[Cl:13])[C:2]=1[Cl:1]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 21188104HCID 21188104, compound

Product 1

HCID 21188072HCID 21188072, compound

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 180AcetoneSolvent

Procedure

To a stirred solution of 5-chloro-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)4-ethynylpyrazole (0.499 g) in acetone (5 ml) was added N-bromosuccinimide (0.244 g) followed by silver nitrate (0.023 g). Stirring was continued for one hour then the reaction mixture was evaporated to dryness. The residue was partitioned between ether and water. The aqueous layer was separated and extracted with ether. The combined organic layers were washed with brine, dried (Na2SO4) and evaporated. The residue was purified by column chromatography on silica gel eluted with dichloromethane: hexane (1:1). Combination and evaporation of suitable fractions followed by recrystallisation from hexane provided the title compound as a white solid m.p. 152.9-153.4° C.

Workup

  1. customthe reaction mixture was evaporated to dryness
  2. customThe residue was partitioned between ether and water
  3. customThe aqueous layer was separated
  4. extractionextracted with ether
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried (Na2SO4)
  7. customevaporated
  8. customThe residue was purified by column chromatography on silica gel
  9. washeluted with dichloromethane: hexane (1:1)
  10. customCombination and evaporation of suitable fractions
  11. customfollowed by recrystallisation from hexane

Sources & evidence

ORD record
ord-4f3853f33742480ea88dda538686ecd1
Source dataset
uspto-grants-2001_07
Patent number
US06255333B1

Reaction notes

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