Bis(2-Methoxyethyl)amine → (2-Fluoro-4-nitro-phenyl)-bis-(2-methoxy-ethyl)-amine

HRID 1971223Notes

Reaction equation

HRID 1971223 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1F.[CH3:12][O:13][CH2:14][CH2:15][NH:16][CH2:17][CH2:18][O:19][CH3:20].C([O-])([O-])=O.[K+].[K+]>CS(C)=O>[F:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1[N:16]([CH2:17][CH2:18][O:19][CH3:20])[CH2:15][CH2:14][O:13][CH3:12]

Participants

5

Reactant 3

HCID 2383Bis(2-Methoxyethyl)amineHCID 11430Potassium CarbonateHCID 1230531,2-Difluoro-4-nitrobenzene

Product 1

HCID 66870223(2-Fluoro-4-nitro-phenyl)-bis-(2-methoxy-ethyl)-amine

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

1.13 g (7.1 mmol) of 3,4-difluoronitrobenzene (Aldrich, Buchs, Switzerland), 1.04 g (7.81 mmol) of bis(2-methoxyethyl)amine (Fluka, Buchs, Switzerland) and 1.96 g (14.2 mmol) of K2CO3 in 7 ml of DMSO are stirred for 1.5 h at rt and then heated at 80° C. for 4 h. The reaction mixture is quenched with H2O and extracted with EtOAc (2×). The organic layers are washed with brine (3×), dried over MgSO4, filtered and evaporated. The residue is purified by flash chromatography on silica gel (hexane-EtOAc 6:1 to 5:1) to give the title compound as a yellow oil. ES-MS: 273 (M+H)+.

Workup

  1. customThe reaction mixture is quenched with H2O
  2. extractionextracted with EtOAc (2×)
  3. washThe organic layers are washed with brine (3×)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is purified by flash chromatography on silica gel (hexane-EtOAc 6:1 to 5:1)

Sources & evidence

ORD record
ord-46c69a5dcc5046ef830491c96264afca
Source dataset
uspto-grants-2013_04
Patent number
US08431592B2

Reaction notes

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