Water → HCID 22494151, compound

HRID 1816578Notes

Reaction equation

HRID 1816578 reaction equation
[CH3:1][O:2][C:3]1[CH:22]=[CH:21][CH:20]=[CH:19][C:4]=1[CH2:5][NH:6][C:7](=[O:18])[C:8]1[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=1.C1N2CN3CN(C2)CN1C3.O.[C:34](=O)(O)[O-:35].[Na+]>FC(F)(F)C(O)=O.C(OCC)(=O)C>[CH:34]([C:20]1[CH:21]=[CH:22][C:3]([O:2][CH3:1])=[C:4]([CH:19]=1)[CH2:5][NH:6][C:7](=[O:18])[C:8]1[CH:13]=[CH:12][C:11]([C:14]([F:16])([F:17])[F:15])=[CH:10][CH:9]=1)=[O:35]

Participants

7

Reactant 4

HCID 962WaterHCID 4101HexamethylenetetramineHCID 516892Sodium BicarbonateHCID 2418241HCID 2418241, compound

Product 1

HCID 22494151HCID 22494151, compound

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 8857Ethyl AcetateSolvent

Procedure

8.7 g of N1-(2-methoxybenzyl)-4-(trifluoromethyl)benzamide was dissolved in 20 ml trifluoroacetic acid, and 3.9 g of hexamethylene tetramine was added, and the mixture was reacted at 85° C. for 3 hours. The reaction solution was returned to room temperature, and water and ethyl acetate were added, and further sodium bicarbonate was added until the pH reached 8. After extracting with ethyl acetate, the extract was washed with brine, dried over anhydrous magnesium sulfate and the solvent was evapoarated. The residue was subjected to silica gel column chromatography, and from fractions eluted with hexane-ethyl acetate (2:1), 4.2 g of N1-(5-formyl-2-methoxybenzyl)-4-(trifluoromethyl)benzamide was obtained.

Workup

  1. customthe mixture was reacted at 85° C. for 3 hours
  2. customwas returned to room temperature
  3. extractionAfter extracting with ethyl acetate
  4. washthe extract was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. washfrom fractions eluted with hexane-ethyl acetate (2:1)

Sources & evidence

ORD record
ord-1420c253485e4472bc9c9fd67aed2c62
Source dataset
uspto-grants-2005_04
Patent number
US06884821B1

Reaction notes

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