Triethylamine → HCID 2418241, compound

HRID 1816577Notes

Reaction equation

HRID 1816577 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][CH:4]=1.[CH3:14][O:15][C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[CH2:18][NH-:19].C(P(=O)(OCC)OCC)#N.C(N(CC)CC)C>CN(C)C=O>[CH3:14][O:15][C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[CH2:18][NH:19][C:7](=[O:9])[C:6]1[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:13])[F:12])=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 99664-(Trifluoromethyl)benzoic acidHCID 76257Diethyl cyanophosphonateHCID 86759679HCID 86759679, compound

Product 1

HCID 2418241HCID 2418241, compoundYield 95.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5.7 g of 4-(trifluoromethyl)benzoic acid and 4.0 g of 2-methoxybenzylamide were dissolved in 100 ml N,N-dimethylformamide, and 4.8 ml diethyl cyanophosphonate and 4.2 ml triethylamine were added under ice-cooling. The reaction mixture was stirred at room temperature for 16 hours, then poured into ice-water and extracted with ethyl acetate. The organic layer was successively washed with 1N hydrochloric acid and 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), 8.7 g of N1-(2-methoxybenzyl)-4-(trifluoromethyl)benzamide was obtained.

Workup

  1. temperaturecooling
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was successively washed with 1N hydrochloric acid and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. washfrom fractions eluted with hexane-ethyl acetate (2:1)

Sources & evidence

ORD record
ord-6e0b6cd4121b45b09f6c1105e9b132f8
Source dataset
uspto-grants-2005_04
Patent number
US06884821B1

Reaction notes

Loading…