2-(Methylamino)ethanol → HCID 23547874, compound

HRID 1398073Notes

Reaction equation

HRID 1398073 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1F.C(=O)([O-])[O-].[K+].[K+].[CH3:18][NH:19][CH2:20][CH2:21][OH:22]>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:19]([CH3:18])[CH2:20][CH2:21][OH:22]

Participants

5

Reactant 3

HCID 80162-(Methylamino)ethanolHCID 11430Potassium CarbonateHCID 1230531,2-Difluoro-4-nitrobenzene

Product 1

HCID 23547874HCID 23547874, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 554 μL (5.0 mmol) of 3,4-difluoronitrobenzene in 10 mL of dimethyl sulfoxide were added 1.38 mg (10.0 mmol) of potassium carbonate and 803 μL (10.0 mmol) of 2-methylaminoethanol, and the mixture was stirred for 1.5 hours at 100° C. The reaction mixture was cooled to room temperature and extracted with ethyl acetate, then, the extract was washed with water and saturated saline solution. After dried over with anhydrous sodium sulfate, the solvent was removed under reduced pressure ant the residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=1/1) to give 1.06 g (99%) of the title compound.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washthe extract was washed with water and saturated saline solution
  4. dry with materialAfter dried over with anhydrous sodium sulfate
  5. customthe solvent was removed under reduced pressure ant the residue
  6. customwas purified by silica gel column chromatography (eluent: hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-f07d892802b4461c98303b7e7136aa6f
Source dataset
uspto-grants-2014_12
Patent number
US08901315B2

Reaction notes

Loading…