Toluene → HCID 85123181, compound

HRID 644463Notes

Reaction equation

HRID 644463 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:4]=[C:5]([CH:14]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:16]=1)[CH2:6][N:7]1[C:11](=[O:12])[CH2:10][S:9][C:8]1=[O:13].C1(C)C=CC=CC=1.[Cl:30][C:31]1[CH:38]=[C:35]([CH:36]=O)[C:34]([OH:39])=[CH:33][CH:32]=1>N1CCCCC1.C(O)(=O)C.O>[Cl:30][C:31]1[CH:32]=[CH:33][C:34]([OH:39])=[C:35]([CH:38]=1)[CH:36]=[C:10]1[S:9][C:8](=[O:13])[N:7]([CH2:6][C:5]2[CH:4]=[C:3]([C:2]([F:1])([F:21])[F:22])[CH:16]=[C:15]([C:17]([F:18])([F:19])[F:20])[CH:14]=2)[C:11]1=[O:12]

Participants

7

Reactant 3

HCID 1140TolueneHCID 124815-Chloro-salicylaldehydeHCID 23069953HCID 23069953, compound

Product 1

HCID 85123181HCID 85123181, compoundYield 62%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 8082PiperidineCatalystHCID 962WaterSolvent

Procedure

A mixture of 3-[3,5-bis(trifluoromethyl)benzyl]thiazolidine-2,4-dione (0.20 g, 0.58 mmol), piperidine (3 drops), acetic acid (3 drops) and toluene (5 mL) was stirred at room temperature for 10 minutes, then 5-chlorosalicylaldehyde (92.3 mg, 0.59 mmol) was added and the mixture was refluxed for 1 hour. After the reaction mixture was cooled to room temperature, it was poured into water and extracted with ethyl acetate. After the ethyl acetate layer was washed with brine and dried over anhydrous sodium sulfate, the residue obtained by evaporation of the solvent under reduced pressure was purified by column chromatography on silica gel (n-hexane:ethyl acetate=2:1→3:2) to give the title compound (173.2 mg, 62.0%) as a light yellow powder.

Workup

  1. temperaturethe mixture was refluxed for 1 hour
  2. temperatureAfter the reaction mixture was cooled to room temperature
  3. extractionextracted with ethyl acetate
  4. washAfter the ethyl acetate layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe residue obtained by evaporation of the solvent under reduced pressure
  7. customwas purified by column chromatography on silica gel (n-hexane:ethyl acetate=2:1→3:2)

Sources & evidence

ORD record
ord-21b4dee6946447bd924890e532bb5954
Source dataset
uspto-grants-2010_04
Patent number
US07700655B2

Reaction notes

Loading…