5-Chlorosalicylic Acid → HCID 57721616, compound

HRID 1777403Notes

Reaction equation

HRID 1777403 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)N.C[CH2:28][N:29]=C=NCCCN(C)C>CN(C1C=CN=CC=1)C.ClCCl>[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)[CH2:28][NH:29][C:7](=[O:9])[C:6]1[CH:10]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=1[OH:11]

Participants

6

Reactant 3

HCID 94475-Chlorosalicylic AcidHCID 9480Benzenamine, 3,5-bis(trifluoromethyl)-HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide

Product 1

HCID 57721616HCID 57721616, compoundYield 38.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To 12 ml of dichloromethane were added 5-chlorosalicylic acid (690 mg, 4 mmol), 3,5-bis(trifluoromethyl)aniline (972 mg, 4 mmol), EDCI (1.2 g, 8 mmol), and DMAP (49 mg, 0.4 mmol) in the presence of argon gas, followed by stirring for 12 hours at room temperature. The mixture was concentrated under reduced pressure, and then 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 (developing solvent: hexane/ethylacetate=1/10) to give 609 mg of the target compound (yield: 38%).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. dissolutiondissolved in 60 ml of ethylacetate
  3. washwhich was washed with water (40 ml×2)
  4. concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-85d27409e4cd494a8ba05504ba46e4d2
Source dataset
uspto-grants-2016_02
Patent number
US09266872B2

Reaction notes

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