Tert-Butylamine → HCID 32217502, compound

HRID 1094447Notes

Reaction equation

HRID 1094447 reaction equation
C([N:5]1[C:13]([C:14]([F:17])([F:16])[F:15])=[CH:12][CH:11]=[C:7]([C:8]([OH:10])=O)[CH:6]1[CH3:18])(C)(C)C.[C:19]([NH2:23])([CH3:22])([CH3:21])[CH3:20].C(N(CC)CC)C.[Cl-].[NH4+]>S(Cl)(Cl)=O>[C:19]([NH:23][C:8](=[O:10])[C:7]1[CH:11]=[CH:12][C:13]([C:14]([F:15])([F:16])[F:17])=[N:5][C:6]=1[CH3:18])([CH3:22])([CH3:21])[CH3:20]

Participants

6

Reactant 4

HCID 6385Tert-ButylamineHCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 66639559N-tert-Butyl-2-methyl-6-trifluoromethyl-nicotinic acid

Product 1

HCID 32217502HCID 32217502, compound

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

N-tert-Butyl-2-methyl-6-trifluoromethyl-nicotinic acid (5.0 g, 24 mmol) is refluxed in 10 mL of thionyl chloride for 3 h and is then concentrated under reduced pressure. The residue is dissolved in toluene and the solvent is removed under reduced pressure. The residue is again dissolved in toluene and the solvent is removed under reduced pressure. The resultant residue is dissolved in 50 mL of dichloromethane and to the solution is added tert-butyl amine (3.8 mL, 49 mmol) and triethylamine (6.8 mL, 49 mmol) and the reaction is allowed to stir overnight. The reaction is then poured into sat. ammonium chloride and extracted three times with dichloromethane. The combined organic phases are then washed with sat. NaHCO3, and brine. The organic layer is then dried over sodium sulfate, filtered, and concentrated under reduced pressure to afford the title compound. Further purification is achieved by trituration from diethyl ether.

Workup

  1. concentrationis then concentrated under reduced pressure
  2. dissolutionThe residue is dissolved in toluene
  3. customthe solvent is removed under reduced pressure
  4. dissolutionThe residue is again dissolved in toluene
  5. customthe solvent is removed under reduced pressure
  6. dissolutionThe resultant residue is dissolved in 50 mL of dichloromethane and to the solution
  7. extractionextracted three times with dichloromethane
  8. washThe combined organic phases are then washed with sat. NaHCO3, and brine
  9. dry with materialThe organic layer is then dried over sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c7774e2ba8794215b7d2b9e00bc03257
Source dataset
uspto-grants-2012_03
Patent number
US08133907B2

Reaction notes

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