Water → Benzenamine, N-(2-methoxyethyl)-N-methyl-4-nitro-2-(trifluoromethyl)-

HRID 1986157Notes

Reaction equation

HRID 1986157 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].C(N(CC)CC)C.[CH3:22][O:23][CH2:24][CH2:25][NH:26][CH3:27].O>CN(C=O)C>[CH3:22][O:23][CH2:24][CH2:25][N:26]([CH3:27])[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 949542-Fluoro-5-nitrobenzotrifluorideHCID 300977(2-Methoxyethyl)(methyl)amine

Product 1

HCID 11471434Benzenamine, N-(2-methoxyethyl)-N-methyl-4-nitro-2-(trifluoromethyl)-

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Dissolved 2-fluoro-5-nitrobenzotrifluoride (250 mg, 1.2 mmol) in DMF (4 mL) and added triethylamine (242 mg, 2.39 mmol). N-(2-methoxyethyl)methylamine (179 mg, 1.32 mmol) was added to the reaction mixture and it was stirred overnight at ambient temperature. The reaction mixture was poured into water and extracted with EtOAc (2×). The combined organic washes were washed with brine and dried over Na2SO4. After concentration the remaining residue was purified by column chromatography (100% CHCl3 to 1:1 MeOH:CHCl3) to give the title compound. MS 265 [M−H]−, 267 [M+H]+.

Workup

  1. extractionextracted with EtOAc (2×)
  2. washThe combined organic washes were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationAfter concentration the remaining residue
  5. customwas purified by column chromatography (100% CHCl3 to 1:1 MeOH:CHCl3)

Sources & evidence

ORD record
ord-d21040849c1a461baadc368087206b99
Source dataset
uspto-grants-2009_06
Patent number
US07547804B2

Reaction notes

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