Hydrochloric Acid → 2-(4-((3-Chloro-5-(trifluoromethyl)-2-pyridinyl)oxy)phenoxy)-N-(3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)phenyl)propanamide

HRID 1655538Notes

Reaction equation

HRID 1655538 reaction equation
[Cl:1][C:2]1[C:3]([O:12][C:13]2[CH:24]=[CH:23][C:16]([O:17][CH:18]([CH3:22])[C:19](Cl)=[O:20])=[CH:15][CH:14]=2)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[Cl:25][C:26]1[CH:27]=[C:28]([CH:30]=[C:31]([Cl:40])[C:32]=1[O:33][C:34]([F:39])([F:38])[CH:35]([F:37])[F:36])[NH2:29].C(N(CC)CC)C.Cl>C(Cl)Cl.CN(C=O)C>[Cl:1][C:2]1[C:3]([O:12][C:13]2[CH:14]=[CH:15][C:16]([O:17][CH:18]([CH3:22])[C:19]([NH:29][C:28]3[CH:30]=[C:31]([Cl:40])[C:32]([O:33][C:34]([F:39])([F:38])[CH:35]([F:37])[F:36])=[C:26]([Cl:25])[CH:27]=3)=[O:20])=[CH:23][CH:24]=2)=[N:4][CH:5]=[C:6]([C:8]([F:9])([F:10])[F:11])[CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 54637633,5-Dichloro-4-(1,1,2,2-tetrafluoroethoxy)anilineHCID 13389070HCID 13389070, compound

Product 1

HCID 197926972-(4-((3-Chloro-5-(trifluoromethyl)-2-pyridinyl)oxy)phenoxy)-N-(3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)phenyl)propanamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3.5 mmol of 2-(4-((3-chloro-5-(trifluoromethyl)-2-pyridinyl)oxy)phenoxy)propionyl chloride in 15 ml of methylene chloride was added dropwise to an ice-cooled solution prepared from 1.22 g (3.5 mmol) of an 80 percent solution of 3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)aniline in DMF, 0.42 g (4.2 mmol) of triethylamine and 40 ml of methylene chloride. The reaction mixture was stirred at room temperature overnight and then poured into a dilute aqueous HCl solution. The organic layer was separated, washed with a saturated aqueous NaHCO3 solution, dried over MgSO4 and evaporated to dryness. The residual material, a gum, was purified by preparative scale liquid chromatography, eluting with an 86:14 hexane:acetone mixture. After removal of the solvent, there was left 1.02 g (47 percent of theoretical) of the above-named product as a light yellow glassy material. The structure of the product was confirmed by its IR and NMR spectrum (NMR Spectrum: (d6 -DMSO); 8.55 (br, m, 1H); 8.45 (br, 1H); 7.9 (s, 2H); 6.6-7.2 (m, 5H); 4.9 (q, 1H); 1.6 (d, 3H). (Compound 2)

Workup

  1. temperaturecooled solution
  2. customThe organic layer was separated
  3. washwashed with a saturated aqueous NaHCO3 solution
  4. dry with materialdried over MgSO4
  5. customevaporated to dryness
  6. customThe residual material, a gum, was purified by preparative scale liquid chromatography
  7. washeluting with an 86:14 hexane
  8. customAfter removal of the solvent, there
  9. waitwas left 1.02 g (47 percent of theoretical) of the above-named product as a light yellow glassy material

Sources & evidence

ORD record
ord-b608e7fb70fd43a2b7d8a4dca1f42830
Source dataset
uspto-grants-1993_10
Patent number
US05250690

Reaction notes

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