Water → N-[4-(trifluoromethyl)phenyl]-2-(5-formyl-2-methoxyphenyl)acetamide

HRID 1816570Notes

Reaction equation

HRID 1816570 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:20])[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:18][CH3:19])=[CH:5][CH:4]=1.C1N2CN3CN(C2)CN1C3.O.[C:34](=O)(O)[O-:35].[Na+]>FC(F)(F)C(O)=O.C(OCC)(=O)C>[F:1][C:2]([F:21])([F:22])[C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:20])[CH2:11][C:12]2[CH:17]=[C:16]([CH:34]=[O:35])[CH:15]=[CH:14][C:13]=2[O:18][CH3:19])=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 962WaterHCID 4101HexamethylenetetramineHCID 516892Sodium BicarbonateHCID 2684094N-[4-(trifluoromethyl)phenyl]-2-(2-methoxyphenyl)acetamide

Product 1

HCID 22493985N-[4-(trifluoromethyl)phenyl]-2-(5-formyl-2-methoxyphenyl)acetamide

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 8857Ethyl AcetateSolvent

Procedure

1.0 g of N-[4-(trifluoromethyl)phenyl]-2-(2-methoxyphenyl)acetamide was dissolved in 10 mg trifluoroacetic acid, and 0.46 g hexamethylene tetramine was added, and the mixture was reacted at 85° C. for 3 hours. The reaction solution was returned to room temperature, water and ethyl acetate were added, and sodium bicarbonate was further added until the pH reached 8. The reaction solution was extracted with ethyl acetate, washed with brine and dried over anhdydrous magnesium sulfate and the solvent was evaporated. The residue was subjected to silica gel column chromatography, to give 0.7 g of N-[4-(trifluoromethyl)phenyl]-2-(5-formyl-2-methoxyphenyl)acetamide as a colorless oil from fractions eluted with hexane-ethyl acetate (1:1).

Workup

  1. customthe mixture was reacted at 85° C. for 3 hours
  2. customwas returned to room temperature
  3. extractionThe reaction solution was extracted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over anhdydrous magnesium sulfate
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-fbf26c4fd6874849ba425fca38a1b74c
Source dataset
uspto-grants-2005_04
Patent number
US06884821B1

Reaction notes

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