Ethyl isobutyrate → HCID 58240230, compound

HRID 2176343Notes

Reaction equation

HRID 2176343 reaction equation
C(OCC)(=O)C(C)C.O.NN.C(S[C:15]([C:25]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=1)=[N:16][C:17]1[C:22]([CH3:23])=[CH:21][CH:20]=[CH:19][C:18]=1[CH3:24])C.[C:32]([NH:37][NH2:38])(=O)[CH:33]([CH3:35])[CH3:34]>C(O)CCC>[CH3:23][C:22]1[CH:21]=[CH:20][CH:19]=[C:18]([CH3:24])[C:17]=1[N:16]1[C:32]([CH:33]([CH3:35])[CH3:34])=[N:37][N:38]=[C:15]1[C:25]1[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=1

Participants

6

Reactant 4

HCID 7342Ethyl isobutyrateHCID 192392-MethylpropanehydrazideHCID 24654Hydrazine hydrate (1:1)HCID 58240249HCID 58240249, compound

Product 1

HCID 58240230HCID 58240230, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent2×

Conditions

Temperature
80 °C

Procedure

First, 2.40 g of ethyl isobutyrate, 10 mL of 1-butanol, and 1.05 g of hydrazine monohydrate (NH2NH2.H2O) were put in a 100 nil, 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, 0.96 g of isobutyric acid hydrazide was added to this mixed solution, and heated and stirred at 130° C. for 15 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-dimethyl-phenyl)-3-(4-fluorophenyl)-5-isopropyl-4H-1,2,4-triazole (abbreviation: HiPrFptz-dmp) was prepared (a white solid, yield: 11%). The synthetic scheme of Step 1 is shown by (a-11).

Workup

  1. temperatureheated
  2. customto be reacted
  3. temperatureheated
  4. stirringstirred at 130° C. for 22 hours
  5. customto be reacted
  6. temperatureheated
  7. stirringstirred at 130° C. for 15 hours
  8. customto be reacted
  9. distillationwas distilled off under a reduced pressure
  10. customThe resulting residue was purified by silica gel column chromatography
  11. concentrationThe resulting fraction was concentrated
  12. customto give a solid
  13. customThis solid was recrystallized from a mixed solvent of toluene and hexane, so that 4-(2,6-dimethyl-phenyl)-3-(4-fluorophenyl)-5-isopropyl-4H-1,2,4-triazole (abbreviation: HiPrFptz-dmp)
  14. customwas prepared (a white solid, yield: 11%)

Sources & evidence

ORD record
ord-011e44283a3141b6b9fb4f68529f9731
Source dataset
uspto-grants-2015_06
Patent number
US09065061B2

Reaction notes

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