Cesium carbonate → N-(4-(1-(((4-(Trifluoromethyl)benzyl)oxy)imino)propyl)phenyl)acetamide

HRID 68314Notes

Reaction equation

HRID 68314 reaction equation
[OH:1][N:2]=[C:3]([C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:15])[CH3:14])=[CH:8][CH:7]=1)[CH2:4][CH3:5].C(=O)([O-])[O-].[Cs+].[Cs+].[F:22][C:23]([F:33])([F:32])[C:24]1[CH:31]=[CH:30][C:27]([CH2:28]Br)=[CH:26][CH:25]=1>CN(C=O)C>[F:22][C:23]([F:32])([F:33])[C:24]1[CH:31]=[CH:30][C:27]([CH2:28][O:1][N:2]=[C:3]([C:6]2[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:15])[CH3:14])=[CH:8][CH:7]=2)[CH2:4][CH3:5])=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 1230621-(Bromomethyl)-4-(trifluoromethyl)benzeneHCID 86699623N-(4-(1-(hydroxyimino)propyl)phenyl)acetamide

Product 1

HCID 86699622N-(4-(1-(((4-(Trifluoromethyl)benzyl)oxy)imino)propyl)phenyl)acetamideYield 94.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-(4-(1-(hydroxyimino)propyl)phenyl)acetamide (6 gm, 0.0291 moles) in DMF (60 mL), cesium carbonate (18.9 gm, 0.0582 moles) and 4-(trifluoromethyl)benzyl bromide (6.96 gm, 0.0291 moles) were added and the reaction mixture was srirred at 25° C. for 3 hours. The reaction mixture was poured into ice cold water and extracted with ethyl acetate. The combined ethyl acetate extract was washed with water & brine, dried over sodium sulphate and evaporated under reduced pressure to yield 10 gm (94%) of product as solid.

Workup

  1. additionThe reaction mixture was poured into ice cold water
  2. extractionextracted with ethyl acetate
  3. extractionThe combined ethyl acetate extract
  4. washwas washed with water & brine
  5. dry with materialdried over sodium sulphate
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-8a2875278ab143aca63f88922068a3a9
Source dataset
uspto-grants-2014_09
Patent number
US08822414B2

Reaction notes

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