5-Chlorosalicylic Acid → Imd-0354

HRID 1777402

Reaction equation

HRID 1777402 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.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[F:12][C:13]([F:25])([F:26])[C:14]1[CH:15]=[C:16]([NH:17][C:7](=[O:9])[C:6]2[CH:10]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[OH:11])[CH:18]=[C:19]([C:21]([F:22])([F:24])[F:23])[CH:20]=1

Participants

6

Reactant 4

HCID 94475-Chlorosalicylic AcidHCID 9480Benzenamine, 3,5-bis(trifluoromethyl)-HCID 24387Phosphorus trichlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 5081913Imd-0354Yield 57%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To 30 ml of toluene were added 5-chlorosalicylic acid (862 mg, 5 mmol), 3,5-bis(trifluoromethyl)aniline (1.37 g, 6 mmol), and phosphoroustrichloride (755 mg, 5.5 mmol) in the presence of argon gas, followed by stirring for 6 hours through heat-reflux. Sodium hydrogen carbonate was added to the mixture to adjust pH to 7, followed by concentration under reduced pressure. The mixture was dissolved in 60 ml of ethylacetate, which was washed with water (40 ml×2). The organic layer was concentrated under reduced pressure, followed by column chromatography to give 1.09 g of the target compound (yield: 57%).

Workup

  1. temperaturethrough heat-reflux
  2. concentrationfollowed by concentration under reduced pressure
  3. dissolutionThe mixture was dissolved in 60 ml of ethylacetate
  4. washwhich was washed with water (40 ml×2)
  5. concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-345a9614066d4029ad26aef33ddc90bf
Source dataset
uspto-grants-2016_02
Patent number
US09266872B2

Linked notes

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