Tert-Butylamine → N-(tert-butyl)-3,5,6-trifluoropyridin-2-amine

HRID 368392Notes

Reaction equation

HRID 368392 reaction equation
F[C:2]1[C:7]([F:8])=[CH:6][C:5]([F:9])=[C:4]([F:10])[N:3]=1.[C:11]([NH2:15])([CH3:14])([CH3:13])[CH3:12]>C(#N)C>[C:11]([NH:15][C:2]1[C:7]([F:8])=[CH:6][C:5]([F:9])=[C:4]([F:10])[N:3]=1)([CH3:14])([CH3:13])[CH3:12]

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 1377492,3,5,6-Tetrafluoropyridine

Product 1

HCID 22121202N-(tert-butyl)-3,5,6-trifluoropyridin-2-amineYield 65.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To 40 ml of acetonitrile were added 11.0 g of 2,3,5,6-tetrafluoropyridine and 18.5 g of t-butylamine, and the mixture was stirred at 60° C. for 3 days, and the solvent and the like were distilled off. To the residue was added 100 ml of chloroform, and the mixture was washed with 50 ml of distilled water. The chloroform layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain 9.7 g of the title compound as a pale yellow oil.

Workup

  1. distillationthe solvent and the like were distilled off
  2. additionTo the residue was added 100 ml of chloroform
  3. washthe mixture was washed with 50 ml of distilled water
  4. dry with materialThe chloroform layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-412fdec089a94f62bfaf9731103381c6
Source dataset
uspto-grants-2000_10
Patent number
US06133284

Reaction notes

Loading…