Water → HCID 66775561, compound

HRID 1645229Notes

Reaction equation

HRID 1645229 reaction equation
[Br:1]N1C(=O)CCC1=O.[Cl:9][C:10]1[C:11]([C:20]2[N:25]3[N:26]=[CH:27][N:28]=[C:24]3[N:23]=[C:22]([CH2:29][CH3:30])[CH:21]=2)=[N:12][CH:13]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:15]=1.O>C(Cl)(Cl)Cl.CC(N=NC(C#N)(C)C)(C#N)C>[Br:1][CH:29]([C:22]1[CH:21]=[C:20]([C:11]2[C:10]([Cl:9])=[CH:15][C:14]([C:16]([F:17])([F:19])[F:18])=[CH:13][N:12]=2)[N:25]2[N:26]=[CH:27][N:28]=[C:24]2[N:23]=1)[CH3:30]

Participants

6

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 25007549HCID 25007549, compound

Product 1

HCID 66775561HCID 66775561, compoundYield 62.5%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 6212ChloroformSolvent

Procedure

4.47 g of N-bromosuccinimide and 50 mg of azobisisobutylonitrile (AIBN) were added to a solution having 5.76 g of 7-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)-5-ethyl-[1,2,4]triazolo[1,5-a]pyrimidine dissolved in 30 mL of chloroform, followed by stirring overnight under reflux with heating. After completion of the reaction, water was added to the reaction liquid, followed by extraction with ethyl acetate, the organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=5/2) to obtain 4.47 g of the desired product as a solid.

Workup

  1. temperatureunder reflux
  2. temperaturewith heating
  3. additionwas added to the reaction liquid
  4. extractionfollowed by extraction with ethyl acetate
  5. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=5/2)

Sources & evidence

ORD record
ord-9fb7c78d48294470b9742ee67870f9ec
Source dataset
uspto-grants-2012_02
Patent number
US08124760B2

Reaction notes

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