Dimethylformamide → HCID 12318721, compound

HRID 2099079Notes

Reaction equation

HRID 2099079 reaction equation
[NH:1]1[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CN(C)C=O.F[C:14]1[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][C:15]=1[N+:24]([O-:26])=[O:25]>O>[N+:24]([C:15]1[CH:16]=[C:17]([C:20]([F:21])([F:22])[F:23])[CH:18]=[CH:19][C:14]=1[N:1]1[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)([O-:26])=[O:25]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 8119AzepaneHCID 677784-Fluoro-3-nitrobenzotrifluoride

Product 1

HCID 12318721HCID 12318721, compoundYield 97.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Hexahydro-1H-azepine (682 μl, 6.05 mmol, commercially available product) was added at 0° C. to an N,N-dimethylformamide (DMF; 2 ml) solution of 1-fluoro-2-nitro-4-(trifluoromethyl)benzene (506 mg, 2.42 mmol, commercially available product). The resulting mixture was warmed to room temperature and stirred for one hour. 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=7/1). Thus, hexahydro-1-[2-nitro-4-(trifluoromethyl)phenyl]-1H-azepine (680 mg, 97.5%) was yielded as an orange-colored solid.

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=7/1)

Sources & evidence

ORD record
ord-3bc62ba0107247a08e4fddb700fc513e
Source dataset
uspto-grants-2009_08
Patent number
US07569536B2

Reaction notes

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