Water → (5-Dimethylamino-2-nitro-4-trifluoromethylphenyl)acetonitrile

HRID 73348

Reaction equation

HRID 73348 reaction equation
[CH3:1][N:2]([CH3:16])[C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[C:12]([F:15])([F:14])[F:13].ClC1C=CC(O[CH2:23][C:24]#[N:25])=CC=1.CC(C)([O-])C.[K+].O>CN(C)C=O>[CH3:1][N:2]([CH3:16])[C:3]1[C:4]([C:12]([F:13])([F:14])[F:15])=[CH:5][C:6]([N+:9]([O-:11])=[O:10])=[C:7]([CH2:23][C:24]#[N:25])[CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 3064442-(4-Chlorophenoxy)acetonitrileHCID 521528N,N-dimethyl-4-nitro-2-(trifluoromethyl)anilineHCID 23665647Potassium tert-butoxide

Product 1

HCID 58437521(5-Dimethylamino-2-nitro-4-trifluoromethylphenyl)acetonitrileYield 9.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of dimethyl-(4-nitro-2-trifluoromethylphenyl)amine (0.95 g) in N,N-dimethylformamide (20 mL) were added (4-chlorophenoxy)acetonitrile (0.75 g) and 1 mol/L potassium tert-butoxide (4.5 mL, in tetrahydrofuran solution) under ice cooling, and this mixture was stirred at the same temperature for 1 hour. This reaction mixture was poured into water, and this mixture was extracted with ethyl acetate. This organic layer was washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate) to give the title compound (0.11 g).

Workup

  1. extractionthis mixture was extracted with ethyl acetate
  2. washThis organic layer was washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-d6372bf02a004b0890cfcdbe6e270fb0
Source dataset
uspto-grants-2014_09
Patent number
US08829040B2

Linked notes

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