Water → 2-(1H-1,2,4-triazol-1-yl)-5-[3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrol-5-yl]benzonitrile

HRID 1873466Notes

Reaction equation

HRID 1873466 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:14](SC)=[N:15][CH2:16][Si](C)(C)C)[CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[N:12][CH:11]=[N:10]1)#[N:2].[Cl:23][C:24]1[CH:29]=[C:28]([C:30]([C:32]([F:35])([F:34])[F:33])=[CH2:31])[CH:27]=[C:26]([Cl:36])[C:25]=1[Cl:37].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>C1COCC1>[N:9]1([C:8]2[CH:7]=[CH:6][C:5]([C:14]3[CH2:31][C:30]([C:28]4[CH:27]=[C:26]([Cl:36])[C:25]([Cl:37])=[C:24]([Cl:23])[CH:29]=4)([C:32]([F:35])([F:34])[F:33])[CH2:16][N:15]=3)=[CH:4][C:3]=2[C:1]#[N:2])[CH:13]=[N:12][CH:11]=[N:10]1

Participants

6

Reactant 4

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 498201551,2,3-Trichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzeneHCID 66820051methyl 3-cyano-4-(1H-1,2,4-triazol-1-yl)-N-[(trimethylsilyl)methyl]benzenecarbimidothioate

Product 1

HCID 441832602-(1H-1,2,4-triazol-1-yl)-5-[3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrol-5-yl]benzonitrileYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-5 °C

Procedure

methyl 3-cyano-4-(1H-1,2,4-triazol-1-yl)-N-[(trimethylsilyl)methyl]benzenecarbimidothioate (0.2 g) and 1,2,3-trichloro-5-[1-(trifluoromethyl)ethenyl]benzene (0.17 g) were dissolved in THF and cooled to −5° C. to be stirring. Additionally a solution of tetrabutylammonium fluoride (0.099 mL of 1.0 M in THF) in THF was added over 10 minutes under argon atmosphere. The reaction mixture was stirred for 30 minutes at the same temperature and returned to room temperature gradually, and then stirred 4 hours. Water was added to the reaction liquor, and aqueous layer was extracted with ethyl acetate. The combined organic layers, were washed with a saturated aqueous brine, subsequently dried over magnesium sulfate. After filtering the reaction mixture, the solvent was distilled off under reduced pressure, and the resulting mixture was purified by silica gel chromatography, to obtain 2-(1H-1,2,4-triazol-1-yl)-5-[3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrol-5-yl]benzonitrile (0.25 g) at a yield of 85%.

Workup

  1. stirringThe reaction mixture was stirred for 30 minutes at the same temperature
  2. customreturned to room temperature
  3. stirringstirred 4 hours
  4. extractionwas extracted with ethyl acetate
  5. washThe combined organic layers, were washed with a saturated aqueous brine
  6. dry with materialsubsequently dried over magnesium sulfate
  7. filtrationAfter filtering the reaction mixture
  8. distillationthe solvent was distilled off under reduced pressure
  9. customthe resulting mixture was purified by silica gel chromatography

Sources & evidence

ORD record
ord-91224d66d7c2418e96285d146f3bd598
Source dataset
uspto-grants-2012_11
Patent number
US08304371B2

Reaction notes

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