Dimethylformamide → N,N-Diethyl-2-nitro-4-(trifluoromethyl)aniline

HRID 2099084Notes

Reaction equation

HRID 2099084 reaction equation
[CH2:1]([NH:3][CH2:4][CH3:5])[CH3:2].CN(C)C=O.F[C:12]1[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][C:13]=1[N+:22]([O-:24])=[O:23]>O>[CH2:1]([N:3]([CH2:4][CH3:5])[C:12]1[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][C:13]=1[N+:22]([O-:24])=[O:23])[CH3:2]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 8021DiethylamineHCID 677784-Fluoro-3-nitrobenzotrifluoride

Product 1

HCID 23149637N,N-Diethyl-2-nitro-4-(trifluoromethyl)anilineYield 98.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Diethylamine (230 μl, 2.22 mmol, commercially available product) was added at room temperature to an N,N-dimethylformamide (DMF; 0.5 ml) solution of 1-fluoro-2-nitro-4-(trifluoromethyl)benzene (211 mg, 1.01 mmol, commercially available product). The resulting mixture was stirred for three hours. Water was added to the mixture, and the resulting mixture was extracted three times with ethyl acetate. The obtained organic layer was washed with a saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (20 g, hexane/ethyl acetate=8/1). Thus, 1-diethylamino-2-nitro-4-(trifluoromethyl)benzene (258 mg, 98.3%) was yielded as an orange-colored oily material.

Workup

  1. extractionthe resulting mixture was extracted three times with ethyl acetate
  2. washThe obtained organic layer was washed with a saturated sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (20 g, hexane/ethyl acetate=8/1)

Sources & evidence

ORD record
ord-8d5adc3d583e44c8ab4e813dc6a95379
Source dataset
uspto-grants-2009_08
Patent number
US07569536B2

Reaction notes

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