Triethylamine → N-[(3-Chloro-5-trifluoromethyl-2-pyridyl)methyl]-3-(2-tolyl)propionamide

HRID 2416013Notes

Reaction equation

HRID 2416013 reaction equation
Cl.[Cl:2][C:3]1[C:4]([CH2:13][NH2:14])=[N:5][CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.C(N(CC)CC)C.[C:22]1([CH3:33])[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[CH2:28][CH2:29][C:30](Cl)=[O:31]>O1CCCC1>[Cl:2][C:3]1[C:4]([CH2:13][NH:14][C:30](=[O:31])[CH2:29][CH2:28][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[CH3:33])=[N:5][CH:6]=[C:7]([C:9]([F:12])([F:10])[F:11])[CH:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 114997441-[3-Chloro-5-(trifluoromethyl)pyridin-2-yl]methanamine hydrochlorideHCID 130292013-(2-Methylphenyl)propanoyl chloride

Product 1

HCID 22637226N-[(3-Chloro-5-trifluoromethyl-2-pyridyl)methyl]-3-(2-tolyl)propionamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of (3-chloro-5-trifluoromethyl-2-pyridyl)methylamine hydrochloride (1 mmol, 0.247 g) in tetrahydrofuran (5 ml) was added triethylamine (2 mmol, 0.202 g) at room temperature and the mixture was stirred at room temperature for 1 hour. The mixture was filtered and the filtrate added to a solution of 3-(2-tolyl)propionyl chloride (1.1 mmol, 0.2 g) in tetrahydrofuran (5 ml) at room temperature. After 4 hours stirring at room temperature the solvent was evaporated and the residue washed with water. The solid was filtered and washed with diethyl ether/light petroleum (1:20) to give the title product, m.p. 152-3° C.

Workup

  1. filtrationThe mixture was filtered
  2. stirringAfter 4 hours stirring at room temperature the solvent
  3. customwas evaporated
  4. washthe residue washed with water
  5. filtrationThe solid was filtered
  6. washwashed with diethyl ether/light petroleum (1:20)

Sources & evidence

ORD record
ord-4244f8e1117e470d9d1b4681bb37d2f4
Source dataset
uspto-grants-2004_11
Patent number
US06821992B1

Reaction notes

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