Ethyl Propionate → HCID 58240196, compound

HRID 2176341Notes

Reaction equation

HRID 2176341 reaction equation
[C:1](OCC)(=O)[CH2:2][CH3:3].O.[NH2:9][NH2:10].C(S[C:14]([C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=1)=[N:15][C:16]1[C:21]([CH3:22])=[CH:20][CH:19]=[CH:18][C:17]=1[CH3:23])C>C(O)CCC>[CH3:23][C:17]1[CH:18]=[CH:19][CH:20]=[C:21]([CH3:22])[C:16]=1[N:15]1[C:14]([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)=[N:10][N:9]=[C:1]1[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 7749Ethyl Propionate2×HCID 24654Hydrazine hydrate (1:1)2×HCID 58240249HCID 58240249, compound

Product 1

HCID 58240196HCID 58240196, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent3×

Conditions

Temperature
80 °C

Procedure

First, 1.80 g of ethyl propionate, 10 mL of 1-butanol, and 0.88 g of hydrazine monohydrate (NH2NH2.H2O) were put in a 100 mL three-neck flask, and heated and stirred at 80° C. for 5 hours to be reacted. Then, 5.0 g of N-[(ethylsulfanyl)(4-fluorophenyl)methylidene]-2,6-dimethylaniline was added to this mixed solution, and heated and stirred at 130° C. for 22 hours to be reacted. Further, a solution obtained by heating and stirring 0.90 g of ethyl propionate, 5 mL of 1-butanol, and 0.44 g of hydrazine monohydrate at 80° C. for 3 hours to be reacted was added to the above mixed solution, and the mixed solution was heated and stirred at 130° C. for 8 hours to be reacted. After the reaction, 1-butanol was distilled off under a reduced pressure. The resulting residue was purified by silica gel column chromatography. Ethyl acetate was used as a developing solvent. The resulting fraction was concentrated to give a solid. This solid was recrystallized from a mixed solvent of toluene and hexane, so that 4-(2,6-dimethylphenyl)-3-ethyl-5-(4-fluorophenyl)-4H-1,2,4-triazole (abbreviation: HEFptz-dmp) was prepared (a white solid, yield: 11%). The synthetic scheme of Step 1 is shown by (a-9).

Workup

  1. temperatureheated
  2. customto be reacted
  3. temperatureheated
  4. stirringstirred at 130° C. for 22 hours
  5. customto be reacted
  6. customFurther, a solution obtained
  7. temperatureby heating
  8. customto be reacted
  9. additionwas added to the above mixed solution
  10. temperaturethe mixed solution was heated
  11. stirringstirred at 130° C. for 8 hours
  12. customto be reacted
  13. distillationwas distilled off under a reduced pressure
  14. customThe resulting residue was purified by silica gel column chromatography
  15. concentrationThe resulting fraction was concentrated
  16. customto give a solid
  17. customThis solid was recrystallized from a mixed solvent of toluene and hexane, so that 4-(2,6-dimethylphenyl)-3-ethyl-5-(4-fluorophenyl)-4H-1,2,4-triazole (abbreviation: HEFptz-dmp)
  18. customwas prepared (a white solid, yield: 11%)

Sources & evidence

ORD record
ord-1203eb6e04494b9a9d50fdba664830ee
Source dataset
uspto-grants-2015_06
Patent number
US09065061B2

Reaction notes

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