N-Ethylaniline → HCID 28830712, compound

HRID 475928Notes

Reaction equation

HRID 475928 reaction equation
[CH2:1]([NH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:2].[H-].[Na+].[C:12]([O:15][CH2:16]Br)(=[O:14])[CH3:13]>CN(C=O)C>[CH2:1]([N:3]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH2:13][C:12]([O:15][CH3:16])=[O:14])[CH3:2]

Participants

5

Reactant 3

HCID 7670N-EthylanilineHCID 24758Sodium hydrideHCID 68536Bromomethyl acetate

Product 1

HCID 28830712HCID 28830712, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-Ethylaniline 5 (2 g, 16.52 mmol) was added to a stirred suspension of sodium hydride (436 mg, 18.17 mmol) in DMF (20 ml) at ambient temperature under argon. After 45 minutes, bromomethyl acetate (3.02 g, 18.17 mmol) was added and the reaction mixture was stirred for 22 hr. DMF was removed under reduced pressure and the residue was treated with ethyl acetate (60 ml) and water (50 ml). The organic extract was washed with saturated brine (50 ml), dried (Na2SO4), filtered and evaporated to give crude Methyl 2-(ethylphenylamino) acetate 7 as liquid (3.06 g, 96%).

Workup

  1. customDMF was removed under reduced pressure
  2. additionthe residue was treated with ethyl acetate (60 ml) and water (50 ml)
  3. extractionThe organic extract
  4. washwas washed with saturated brine (50 ml)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-cb5f8825927941c09a0498b2686080bc
Source dataset
uspto-grants-2014_01
Patent number
US08637658B2

Reaction notes

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