Chlorobenzene → HCID 10318656, compound

HRID 2384319Notes

Reaction equation

HRID 2384319 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, 18.9%) as a white crystal.

Workup

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

Sources & evidence

ORD record
ord-5326c11ab33e482f93fdda82cac62fed
Source dataset
uspto-grants-2012_09
Patent number
US08263657B2

Reaction notes

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