2,2,2-Trifluoroethylhydrazine → HCID 22493388, compound

HRID 1816290Notes

Reaction equation

HRID 1816290 reaction equation
C[N:2]([CH:4]=[N:5][C:6](=O)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N+:13]([O-:15])=[O:14])C.[F:17][C:18]([F:23])([F:22])[CH2:19][NH:20]N>C(O)(=O)C.C(O)CCC>[F:17][C:18]([F:23])([F:22])[CH2:19][N:20]1[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[N+:13]([O-:15])=[O:14])=[N:5][CH:4]=[N:2]1

Participants

5

Reactant 2

HCID 787402,2,2-TrifluoroethylhydrazineHCID 22493374HCID 22493374, compound

Product 1

HCID 22493388HCID 22493388, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 2631-ButanolSolvent

Procedure

N-[(Dimethylamino)methylene]-2-nitrobenzamide (1.0 g, 4.5 mmol) in acetic acid (25 mL) and n-butanol (15 mL) was treated with 70% aqueous 1,1,1-trifluoroethylhydrazine (1 mL, 11.3 mmol), and heated to reflux for 2 hours, at which time the volume was reduced by ˜25 mL by distillation. The remaining solvent was removed in vacuo, and the residue chromatographed on silica eluting with 3:1-1:1 hexane:ethyl acetate to afford 1-(2,2,2-trifluoroethyl)-5-(2-nitrophenyl)-1,2,4-triazole, which was reduced as in Example 64 to give crude 1-(2,2,2-trifluoroethyl)-5-(2-aminophenyl)-1,2,4-triazole (430 mg).

Workup

  1. temperatureheated
  2. temperatureto reflux for 2 hours, at which time the volume
  3. distillationwas reduced by ˜25 mL by distillation
  4. customThe remaining solvent was removed in vacuo
  5. customthe residue chromatographed on silica eluting with 3:1-1:1 hexane

Sources & evidence

ORD record
ord-96eb4996b8f247f5bb71698977331be9
Source dataset
uspto-grants-2005_04
Patent number
US06884801B1

Reaction notes

Loading…