Ethyl trifluoroacetate → HCID 20322685, compound

HRID 259529Notes

Reaction equation

HRID 259529 reaction equation
[F:1][C:2]([F:9])([F:8])[C:3](OCC)=O.O.[NH2:11][NH2:12].C(O[C:16](=[N:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH3:17])C>CO>[CH3:17][C:16]1[N:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:3]([C:2]([F:1])([F:8])[F:9])=[N:12][N:11]=1

Participants

5

Reactant 3

HCID 9794Ethyl trifluoroacetateHCID 24654Hydrazine hydrate (1:1)HCID 12574593HCID 12574593, compound

Product 1

HCID 20322685HCID 20322685, compoundYield 51.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl trifluoroacetate (4.3 g) was added to hydrazine hydrate (1.5 g, 99-100%) in methanol (30 ml) at 5°-10° and stirred for 15 min. Ethyl-N-phenylacetimidate (3.9 g) was added keeping the temperature below 10° for 1 hr and then at room temperature for another hour. The mixture was evaporated to dryness under reduced pressure and the residue heated at 90°-100° with glacial acetic acid (50 ml) for 1 hr. Evaporation under reduced pressure and crystallization of the residue from methyl cyclohexane gave 3-methyl-4-phenyl-5-trifluoromethyl-1,2,4-triazole (2.8 g, 41.2%) m.p. 118°. (Found: C, 52.73%; H, 3.72%; F, 25.3%; N, 18.78%. C10H8F3N4 requires: C, 52.87%; H, 3.55%; F, 25.1%; N, 18.50%). δ(CDCl3): 7.47 (5H, m); 2.33 (3H, s). m/e, 227.

Workup

  1. customthe temperature below 10°
  2. customfor 1 hr
  3. waitat room temperature for another hour
  4. customThe mixture was evaporated to dryness under reduced pressure
  5. temperaturethe residue heated at 90°-100° with glacial acetic acid (50 ml) for 1 hr
  6. customEvaporation
  7. customunder reduced pressure and crystallization of the residue from methyl cyclohexane

Sources & evidence

ORD record
ord-4471bd3ffcd548a2986497c6af2c149c
Source dataset
uspto-grants-1977_07
Patent number
US04038405

Reaction notes

Loading…