Ethyl trifluoroacetate → HCID 67387231, compound

HRID 1468589Notes

Reaction equation

HRID 1468589 reaction equation
[F:1][C:2]([F:9])([F:8])[C:3](OCC)=O.O.[NH2:11][NH2:12].[C:13]1([N:19]=[C:20]([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)SCC)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(O)CCC>[F:30][C:27]1[CH:28]=[CH:29][C:24]([C:20]2[N:19]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:3]([C:2]([F:1])([F:8])[F:9])=[N:12][N:11]=2)=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 9794Ethyl trifluoroacetateHCID 24654Hydrazine hydrate (1:1)HCID 58426406HCID 58426406, compound

Product 1

HCID 67387231HCID 67387231, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

First, 3.0 g of ethyl trifluoroacetate and 10 mL of 1-butanol were put in a 100 mL three-neck flask and stirred with being cooled with ice for 10 minutes. After the stirring, 1.1 g of hydrazine monohydrate was added to this mixed solution, and the solution was stirred for 30 minutes while the temperature was increased to room temperature. Then, 5.1 g of ethyl N-phenyl-4-fluorobenzenecarboximidothioate was added to this reacted solution, and the reacted solution was heated and refluxed at 130° C. for 5 hours. After the reflux, 1-butanol was distilled off under a reduced pressure to give an oily substance. The given oily substance was purified by silica gel column chromatography. A mixed solvent of toluene:ethyl acetate=4:1 (v/v) was used as a developing solvent. The obtained fraction was concentrated to give a solid. This solid was recrystallized from a mixed solvent of ethanol and hexane, so that 3-(4-fluorophenyl)-4-phenyl-5-trifluoromethyl-4H-1,2,4-triazole (abbreviation: HCF3Fptz) was prepared (a white solid, yield: 27%). The synthetic scheme of Step 1 is shown by (a-3).

Workup

  1. temperaturewith being cooled with ice for 10 minutes
  2. stirringthe solution was stirred for 30 minutes while the temperature
  3. temperaturethe reacted solution was heated
  4. temperaturerefluxed at 130° C. for 5 hours
  5. distillationAfter the reflux, 1-butanol was distilled off under a reduced pressure
  6. customto give an oily substance
  7. customThe given oily substance was purified by silica gel column chromatography
  8. concentrationThe obtained fraction was concentrated
  9. customto give a solid
  10. customThis solid was recrystallized from a mixed solvent of ethanol and hexane, so that 3-(4-fluorophenyl)-4-phenyl-5-trifluoromethyl-4H-1,2,4-triazole (abbreviation: HCF3Fptz)
  11. customwas prepared (a white solid, yield: 27%)

Sources & evidence

ORD record
ord-23c646ee14ba47bca3522b9818250c4e
Source dataset
uspto-grants-2015_04
Patent number
US09005773B2

Reaction notes

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