Triethylamine → HCID 22637223, compound

HRID 2416008Notes

Reaction equation

HRID 2416008 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][C:11]([OH:13])=O)([O-:3])=[O:2].P(Cl)(Cl)(Cl)=O.Cl.[Cl:20][C:21]1[C:22]([CH2:31][NH2:32])=[N:23][CH:24]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:26]=1.C(N(CC)CC)C>C1(C)C=CC=CC=1>[Cl:20][C:21]1[C:22]([CH2:31][NH:32][C:11](=[O:13])[CH2:10][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N+:1]([O-:3])=[O:2])=[N:23][CH:24]=[C:25]([C:27]([F:30])([F:28])[F:29])[CH:26]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 77337(2-Nitrophenyl)acetic acidHCID 114997441-[3-Chloro-5-(trifluoromethyl)pyridin-2-yl]methanamine hydrochloride

Product 1

HCID 22637223HCID 22637223, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a stirred suspension of 2-nitrophenylacetic acid (0.36 g) in dry toluene (5 ml) at room temperature was added phosphoryl chloride (0.37 g) and stirring was continued overnight. Meanwhile a solution of the amine was prepared, (3-Chloro-5-trifluoromethyl-2-pyridyl)methylamine hydrochloride (0.49 g) in dry toluene (5 ml) and triethylamine (1.23 g) was stirred at room temperature for 1 hour and then filtered. The solid was washed with dry toluene and the combined filtrates were added dropwise to the above suspension of acid chloride with ice-cooling. After addition, the mixture was stirred at room temperature overnight. Dichloromethane was added and the mixture was washed with water. The aqueous layer was separated and back-extracted with dichloromethane. The combined organic extracts were washed with saturated sodium bicarbonate solution, then brine, then dried (MgSO4), and the solvent removed. The resulting residue was purified by silica gel chromatography eluting with ethyl acetate/light petroleum (b.p. 40-60° C.) to give the title product, m.p. 123-4° C.

Workup

  1. filtrationfiltered
  2. washThe solid was washed with dry toluene
  3. additionthe combined filtrates were added dropwise to the above suspension of acid chloride with ice-
  4. temperaturecooling
  5. additionAfter addition
  6. stirringthe mixture was stirred at room temperature overnight
  7. additionDichloromethane was added
  8. washthe mixture was washed with water
  9. customThe aqueous layer was separated
  10. extractionback-extracted with dichloromethane
  11. washThe combined organic extracts were washed with saturated sodium bicarbonate solution
  12. dry with materialbrine, then dried (MgSO4)
  13. customthe solvent removed
  14. customThe resulting residue was purified by silica gel chromatography
  15. washeluting with ethyl acetate/light petroleum (b.p. 40-60° C.)

Sources & evidence

ORD record
ord-330dbff2af3d491fbbd72c30ecbd6c82
Source dataset
uspto-grants-2004_11
Patent number
US06821992B1

Reaction notes

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