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

HRID 1274656
Notes
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Reaction equation

HRID 1274656 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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-795d2d3a90b04db3b7920fb4248969ed
Source dataset
uspto-grants-2000_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06156903

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes