Water → HCID 66775659, compound

HRID 1645230Notes

Reaction equation

HRID 1645230 reaction equation
[Br:1]N1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C.[Cl:21][C:22]1[C:23]([C:32]2[N:37]3[N:38]=[CH:39][N:40]=[C:36]3[N:35]=[C:34]([CH3:41])[CH:33]=2)=[N:24][CH:25]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:27]=1.O>C(Cl)(Cl)(Cl)Cl>[Br:1][CH2:41][C:34]1[CH:33]=[C:32]([C:23]2[C:22]([Cl:21])=[CH:27][C:26]([C:28]([F:29])([F:31])[F:30])=[CH:25][N:24]=2)[N:37]2[N:38]=[CH:39][N:40]=[C:36]2[N:35]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 250075467-[3-Chloro-5-(trifluoromethyl)pyridin-2-yl]-5-methyl[1,2,4]triazolo[1,5-a]pyrimidine

Product 1

HCID 66775659HCID 66775659, compoundYield 13.7%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

312 mg of N-bromosuccinimide and 13 mg of azobisisobutylonitrile (AIBN) were added to a solution having 500 mg of 7-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine dissolved in 3 mL of carbon tetrachloride, 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=7/3) to obtain 86 mg of the desired product.

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=7/3)

Sources & evidence

ORD record
ord-1c68326510274908b4e5ed1bf122bf4f
Source dataset
uspto-grants-2012_02
Patent number
US08124760B2

Reaction notes

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