Ethanol → 3-(2,6-Dimethylphenylamino)-2-butanone

HRID 2286036Notes

Reaction equation

HRID 2286036 reaction equation
C[N:2](C)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5]C=1.Br[CH:11]([CH3:15])[C:12](=[O:14])[CH3:13].[C:16](=O)(O)[O-].[Na+].[CH2:21](O)[CH3:22]>ClCCl>[CH3:16][C:8]1[CH:7]=[CH:6][CH:5]=[C:21]([CH3:22])[C:3]=1[NH:2][CH:11]([CH3:15])[C:12](=[O:14])[CH3:13]

Participants

6

Reactant 4

HCID 702EthanolHCID 949N,N-DimethylanilineHCID 131422-Butanone, 3-bromo-HCID 516892Sodium Bicarbonate

Product 1

HCID 124914753-(2,6-Dimethylphenylamino)-2-butanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 121 g (1 mol) dimethylaniline, 149 g (1 mol) 3-bromo-2-butanone and 126 g (1.5 mol) sodium bicarbonate in 500 ml ethanol was stirred at 60°-70° C. for about 18 hours. The reaction mixture was filtered and the filtrate evaporated under reduced pressure to give an oil. The oil was taken up in dichloromethane, dried over magnesium sulfate, treated with silica, filtered and evaporated under reduced pressure to give 174.8 g 3-(2,6-dimethylphenylamino)-2-butanone as a light amber oil. The infrared spectrum of the product showed strong carbonyl absorption at 5.8 microns.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate evaporated under reduced pressure
  3. customto give an oil
  4. dry with materialdried over magnesium sulfate
  5. additiontreated with silica
  6. filtrationfiltered
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-59f983e55cd947aaa3e54475e51f6535
Source dataset
uspto-grants-1982_04
Patent number
US04326077

Reaction notes

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