Salicylic Acid → N-[2,5-Bis(trifluoromethyl)phenyl]-2-hydroxybenzamide

HRID 1865396Notes

Reaction equation

HRID 1865396 reaction equation
[C:1]([OH:10])(=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[F:11][C:12]([F:25])([F:24])[C:13]1[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][C:14]=1[NH2:15].P(Cl)(Cl)Cl.ClC1C=CC=CC=1>C(OCC)(=O)C>[OH:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[C:1]([NH:15][C:14]1[CH:16]=[C:17]([C:20]([F:21])([F:22])[F:23])[CH:18]=[CH:19][C:13]=1[C:12]([F:11])([F:24])[F:25])=[O:10]

Participants

6

Reactant 4

HCID 338Salicylic AcidHCID 7964ChlorobenzeneHCID 24387Phosphorus trichlorideHCID 7198182,5-Bis(trifluoromethyl)aniline

Product 1

HCID 23070350N-[2,5-Bis(trifluoromethyl)phenyl]-2-hydroxybenzamideYield 48.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of salicylic acid (6.90 g, 50 mmol), 2,5-bis(trifluoromethyl)-aniline (11.46 g, 50 mmol), phosphorus trichloride(2.18 ml, 25 mmol) and chlorobenzene(150 mL) was refluxed for 4 hours. After the reaction mixture was cooled to room temperature, it was diluted with ethyl acetate. The organic layer was washed with water and brine, and dried over magnesium sulfate. The residue obtained by evaporation of the solvent under reduced pressure was washed with n-hexane to give the title compound(8.4 g, 47.8%) as a white solid.

Workup

  1. temperaturewas refluxed for 4 hours
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customThe residue obtained by evaporation of the solvent under reduced pressure
  5. washwas washed with n-hexane

Sources & evidence

ORD record
ord-b84311830763498d9814de048cd2ec16
Source dataset
uspto-grants-2009_12
Patent number
US07626042B2

Reaction notes

Loading…