Ethyl Acetoacetate → HCID 178429171, compound

HRID 591236Notes

Reaction equation

HRID 591236 reaction equation
[F:1][C:2]([F:10])([F:9])[C:3]1[NH:4][C:5]([NH2:8])=[N:6][N:7]=1.[C:11](OCC)(=[O:16])[CH2:12][C:13]([CH3:15])=O>C(O)(=O)C>[CH3:15][C:13]1[CH:12]=[C:11]([OH:16])[N:6]2[N:7]=[C:3]([C:2]([F:10])([F:9])[F:1])[N:4]=[C:5]2[N:8]=1

Participants

4

Reactant 2

HCID 8868Ethyl AcetoacetateHCID 178509149HCID 178509149, compound

Product 1

HCID 178429171HCID 178429171, compoundYield 52.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a well-stirred solution of 5-(trifluoromethyl)-4H-1,2,4-triazol-3-amine (1 g, 6.58 mmol) in 15-20 mL glacial acetic acid, was added ethyl acetoacetate (2.57 g or 2.5 mL, 19.77 mmol) and the reaction mixture was refluxed for 6-6.5 h. Reaction progress was monitored by TLC. After completion, the reaction mixture was brought to room temperature and the excess glacial acetic acid was evaporated in vacuo. The light pinkish white solid, thus obtained, was filtered off, washed with dichloromethane and dried to yield 0.750 g (52.3%) of the titled compound.

Workup

  1. temperaturethe reaction mixture was refluxed for 6-6.5 h
  2. customReaction progress
  3. customwas brought to room temperature
  4. customthe excess glacial acetic acid was evaporated in vacuo
  5. customThe light pinkish white solid, thus obtained
  6. filtrationwas filtered off
  7. washwashed with dichloromethane
  8. customdried

Sources & evidence

ORD record
ord-67e743aadb334aa78bc061565f7e4518
Source dataset
uspto-grants-2016_01
Patent number
US09238653B2

Reaction notes

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