3-(Trifluoromethyl)phenylglyoxal → HCID 67050195, compound

HRID 2103836Notes

Reaction equation

HRID 2103836 reaction equation
[CH3:1][NH:2][N:3]=[CH:4][C:5](=[O:7])[CH3:6].O=[C:9]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=1)[CH:10]=[O:11].C(Cl)(Cl)Cl.CO>C(O)(=O)C>[OH:11][C:10]1[C:4]([C:5](=[O:7])[CH3:6])=[N:3][N:2]([CH3:1])[C:9]=1[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=1

Participants

5

Reactant 3

HCID 27832843-(Trifluoromethyl)phenylglyoxalHCID 21584188Chloroform methanolHCID 727702682-Oxopropanal methylhydrazone

Product 1

HCID 67050195HCID 67050195, compoundYield 11.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

2-Oxopropanal methylhydrazone (7.49 mmol, 750 mg) and (oxo)[3-trifluoromethylphenyl]acetaldehyde (7.0 mmol, 1.42 g) synthesized in Reference Synthetic Example 8 were dissolved in acetic acid (20 mL) and stirred at 100° C. for 4 hours. Then, the solvent was evaporated, and the residue was dried by means of a vacuum pump and purified by silica gel column chromatography (n-hexane/ethyl acetate=2/1) and then by silica gel thin layer chromatography (chloroform/methanol=30/1) to give the desired product as a reddish yellow liquid (221 mg, yield 11%).

Workup

  1. customThen, the solvent was evaporated
  2. customthe residue was dried by means of a vacuum pump
  3. custompurified by silica gel column chromatography (n-hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-39e4c563759d43899800eced9d93bb02
Source dataset
uspto-grants-2009_08
Patent number
US07576115B2

Reaction notes

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