Toluene → Imd-0354

HRID 1865349

Reaction equation

HRID 1865349 reaction equation
[Cl:1][C:2]1[CH:10]=[C:6]([C:7]([OH:9])=O)[C:5]([OH:11])=[CH:4][CH:3]=1.[F:12][C:13]([F:26])([F:25])[C:14]1[CH:15]=[C:16]([CH:18]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:20]=1)[NH2:17].P(Cl)(Cl)Cl.C1(C)C=CC=CC=1>C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([CH:10]=1)[C:7]([NH:17][C:16]1[CH:18]=[C:19]([C:21]([F:22])([F:23])[F:24])[CH:20]=[C:14]([C:13]([F:12])([F:25])[F:26])[CH:15]=1)=[O:9]

Participants

6

Reactant 4

HCID 1140TolueneHCID 94475-Chlorosalicylic AcidHCID 9480Benzenamine, 3,5-bis(trifluoromethyl)-HCID 24387Phosphorus trichloride

Product 1

HCID 5081913Imd-0354Yield 85.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5-chlorosalicylic acid(6.90 g, 40 mmol), 3,5-bis(trifluoromethyl)aniline(9.16 g, 40 mmol), phosphorus trichloride(1.74 mL, 20 mmol) and toluene(80 mL) was refluxed for 3 hours under argon atmosphere. After the reaction mixture was cooled to room temperature, it was diluted with ethyl acetate (240 mL). After the ethyl acetate layer was washed successively with water and brine, dried over anhydrous magnesium sulfate, the residue obtained by evaporation of the solvent under reduced pressure was purified by column chromatography on silica gel (n-hexane:ethyl acetate=4:1) to give the title compound (13.12 g, 85.5%) as a light yellow solid.

Workup

  1. temperaturewas refluxed for 3 hours under argon atmosphere
  2. washAfter the ethyl acetate layer was washed successively with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe residue obtained by evaporation of the solvent under reduced pressure
  5. customwas purified by column chromatography on silica gel (n-hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-15e5a58d6dda499799ed9adf297e061d
Source dataset
uspto-grants-2009_12
Patent number
US07626042B2

Linked notes

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