2,2,2-Trifluoroethylhydrazine → 5-(2-methyl-prop enyl)-3-pyrrolidin-1-yl-1-(2,2,2-trifluoro-ethyl)-1H-[1,2,4]triazole

HRID 1054931Notes

Reaction equation

HRID 1054931 reaction equation
[CH3:1][C:2]([CH3:15])=[CH:3][C:4](/[N:6]=[C:7](/[N:10]1[CH2:14][CH2:13][CH2:12][CH2:11]1)\SC)=O.[F:16][C:17]([F:22])([F:21])[CH2:18][NH:19][NH2:20]>C(OCC)(=O)C>[CH3:1][C:2]([CH3:15])=[CH:3][C:4]1[N:19]([CH2:18][C:17]([F:22])([F:21])[F:16])[N:20]=[C:7]([N:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)[N:6]=1

Participants

4

Reactant 2

HCID 787402,2,2-TrifluoroethylhydrazineHCID 178503950HCID 178503950, compound

Product 1

HCID 900167765-(2-methyl-prop enyl)-3-pyrrolidin-1-yl-1-(2,2,2-trifluoro-ethyl)-1H-[1,2,4]triazoleYield 52.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of (Z)-methyl N-3-methylbut-2-enoylpyrrolidine-1-carbimidothioate (2.515 g, 11.1 mmol, Eq: 1.00) and (2,2,2-trifluoroethyl)hydrazine (5 g, 30.7 mmol, Eq: 2.76) was stirred for 1 hour at 100° C. The mixture was dissolved in ethyl acetate and washed with water 3 times and once with brine. The organic layer was separated, dried over magnesium sulfate, filtrated and evaporated affording 5-(2-methyl-prop enyl)-3-pyrrolidin-1-yl-1-(2,2,2-trifluoro-ethyl)-1H-[1,2,4]triazole (1.599 g/52.5%) as an off-white waxy solid. MS: m/e=275.4 (M+H+)

Workup

  1. washwashed with water 3 times and once with brine
  2. customThe organic layer was separated
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltrated
  5. customevaporated

Sources & evidence

ORD record
ord-2dbccd892a6b48f1b625b350d1afa5f5
Source dataset
uspto-grants-2016_07
Patent number
US09394311B2

Reaction notes

Loading…