Pyridine → N-(3,4-Dichlorophenyl)-N-methyl-3-oxobutanamide

HRID 648756

Reaction equation

HRID 648756 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[Cl:10])[NH:5][CH3:6].N1C=CC=CC=1.[CH2:17]=[C:18]1[O:22][C:20](=[O:21])[CH2:19]1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[Cl:10])[N:5]([CH3:6])[C:20](=[O:21])[CH2:19][C:18]([CH3:17])=[O:22]

Participants

5

Reactant 3

HCID 1049PyridineHCID 12661DiketeneHCID 28009313,4-Dichloro-N-methylaniline

Product 1

HCID 13822492N-(3,4-Dichlorophenyl)-N-methyl-3-oxobutanamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Dissolved in toluene were 3.5 g (0.02 mole) of 3,4-dichloro-N-methylaniline and a catalytic amount of pyridine, followed by a dropwise addition of 1.9 g (0.022 mole) of diketene at 50° C. After completion of the the dropwise addition, the resultant mixture was heated under reflux for 3 hours. The reaction mixture was cooled, and its organic layer was then washed with water, water, a 10% aqueous solution of hydrochloric acid and a 5% aqueous solution of sodium hydrogencarbonate in order. The thus-washed organic solution was dried and concentrated to obtain 3',4'-dichloro-N-methylacetoacetoanilide.

Workup

  1. additionAfter completion of the the dropwise addition
  2. temperatureunder reflux for 3 hours
  3. temperatureThe reaction mixture was cooled
  4. washits organic layer was then washed with water, water
  5. customThe thus-washed organic solution was dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8d4a5e6eb18d4834a8e1de7d28d4ce2d
Source dataset
uspto-grants-1988_04
Patent number
US04736038

Linked notes

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