4-Hydroxybenzaldehyde → N-[4-[(4-formylphenyl)oxy]-2-nitro-6-(trifluoromethyl)phenyl]acetamide

HRID 547643Notes

Reaction equation

HRID 547643 reaction equation
F[C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[C:5]([NH:12][C:13](=[O:15])[CH3:14])=[C:4]([N+:16]([O-:18])=[O:17])[CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].[OH:25][C:26]1[CH:33]=[CH:32][C:29]([CH:30]=[O:31])=[CH:28][CH:27]=1.O>CS(C)=O>[CH:30]([C:29]1[CH:32]=[CH:33][C:26]([O:25][C:2]2[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[C:5]([NH:12][C:13](=[O:15])[CH3:14])=[C:4]([N+:16]([O-:18])=[O:17])[CH:3]=2)=[CH:27][CH:28]=1)=[O:31]

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 962WaterHCID 10796Cesium carbonateHCID 10778132N-[4-fluoro-2-nitro-6-(trifluoromethyl)phenyl]acetamide

Product 1

HCID 57585843N-[4-[(4-formylphenyl)oxy]-2-nitro-6-(trifluoromethyl)phenyl]acetamideYield 44%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of N-[4-fluoro-2-nitro-6-(trifluoromethyl)phenyl]acetamide (1.5 g, 5.63 mmol), Cs2CO3 (4.59 g, 14.09 mmol), and 4-hydroxybenzaldehyde (0.757 g, 6.20 mmol) in dimethylsulfoxide (10 mL) was heated to 80 degrees Centigrade for 2 h and then cooled. H2O was added and the organics extracted using ethyl acetate (2×50 mL). The combined organics were then washed 1× brine and then dried (Na2SO4), filtered and concentrated. Chromatography on silica gel, using 2:1 hexanes/ethyl acetate eluted N-[4-[(4-formylphenyl)oxy]-2-nitro-6-(trifluoromethyl)phenyl]acetamide as an orange solid. (0.922 g; 44% yield).

Workup

  1. temperaturecooled
  2. extractionthe organics extracted
  3. washThe combined organics were then washed 1× brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. washeluted N-[4-[(4-formylphenyl)oxy]-2-nitro-6-(trifluoromethyl)phenyl]acetamide as an orange solid

Sources & evidence

ORD record
ord-90f20fde7d9c4711894da44cca126bbd
Source dataset
uspto-grants-2011_05
Patent number
US07939528B2

Reaction notes

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