Ethanol → HCID 85135010, compound

HRID 644455Notes

Reaction equation

HRID 644455 reaction equation
[Cl:1][C:2]1[CH:11]=[C:6]([C:7]([NH:9][NH2:10])=[O:8])[C:5]([OH:12])=[CH:4][CH:3]=1.[F:13][C:14]([F:28])([F:27])[C:15]1[CH:16]=[C:17]([CH:20]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:22]=1)[CH:18]=O.C(O)C>S(=O)(=O)(O)O.O>[F:13][C:14]([F:27])([F:28])[C:15]1[CH:16]=[C:17]([CH:20]=[C:21]([C:23]([F:26])([F:24])[F:25])[CH:22]=1)[CH:18]=[N:10][NH:9][C:7](=[O:8])[C:6]1[C:5](=[CH:4][CH:3]=[C:2]([Cl:1])[CH:11]=1)[OH:12]

Participants

6

Reactant 3

HCID 702EthanolHCID 1362473,5-Bis(trifluoromethyl)benzaldehyde2×HCID 27948705-chloro-2-hydroxybenzohydrazide

Product 1

HCID 85135010HCID 85135010, compoundYield 76.8%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 962WaterSolvent

Procedure

A mixture of 5-chlorosalicylhydrazide (213.9 mg, 1.2 mmol), 3,5-bis(trifluoromethyl)benzaldehyde (190 μL, 1.2 mmol), concentrated sulfuric acid (3 drops) and ethanol (5 mL) was refluxed for 30 minutes. 3,5-Bis(trifluoromethyl)benzaldehyde (100 μL, 0.61 mmol) was added and the mixture was refluxed for further 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, dried over 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=3:1→2:1) and washed with n-hexane under suspension to give the title compound (362.6 mg, 76.8%) as a white powder.

Workup

  1. temperaturewas refluxed for 30 minutes
  2. temperaturethe mixture was refluxed for further 1 hour
  3. extractionextracted with ethyl acetate
  4. washAfter the ethyl acetate layer was washed with brine
  5. dry with materialdried over 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=3:1→2:1)
  8. washwashed with n-hexane under suspension

Sources & evidence

ORD record
ord-3582a5429fc243f3abef8f6b9f0c8091
Source dataset
uspto-grants-2010_04
Patent number
US07700655B2

Reaction notes

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