Chlorobenzene → HCID 10318656, compound

HRID 421016Notes

Reaction equation

HRID 421016 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:27])([F:26])[C:14]1[CH:15]=[C:16]([CH:19]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:21]=1)[NH:17][CH3:18].P(Cl)(Cl)Cl.ClC1C=CC=CC=1>CCCCCC>[F:12][C:13]([F:26])([F:27])[C:14]1[CH:15]=[C:16]([N:17]([CH3:18])[C:7](=[O:9])[C:6]2[CH:10]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[OH:11])[CH:19]=[C:20]([C:22]([F:23])([F:25])[F:24])[CH:21]=1

Participants

6

Reactant 4

HCID 7964ChlorobenzeneHCID 94475-Chlorosalicylic AcidHCID 24387Phosphorus trichlorideHCID 13803020N-Methyl-3,5-bis(trifluoromethyl)aniline

Product 1

HCID 10318656HCID 10318656, compoundYield 18.9%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A mixture of 5-chlorosalicylic acid (173 mg, 1 mmol), 3,5-bis(trifluoromethyl)-N-methylaniline (243 mg, 1 mmol). phosphorus trichloride (44 μl, 0.5 mmol) and monochlorobenzene (5 mL) was refluxed for 3 hours under argon atmosphere. After the reaction mixture was cooled to room temperature, n-hexane (50 mL) was added, and the separated crude crystal was filtered and dissolved in ethyl acetate (50 mL). After the ethyl acetate solution was washed with water and brine one after another, dried over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure. The obtained residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=2:1) to give the title compound (75 mg, 13.9%) as a white crystal.

Workup

  1. customthe separated crude crystal
  2. filtrationwas filtered
  3. dissolutiondissolved in ethyl acetate (50 mL)
  4. washAfter the ethyl acetate solution was washed with water and brine one after another,
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-5c5e690c74954fa38b7ab31ff2910c4c
Source dataset
uspto-grants-2012_01
Patent number
US08097759B2

Reaction notes

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