Acetic Acid → N-isopropyl-4'-chloroacetoacetanilide

HRID 224497Notes

Reaction equation

HRID 224497 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([NH:6][CH:7]([CH3:9])[CH3:8])=[CH:4][CH:3]=1.C(O)(=O)C.[CH2:16]=[C:17]1[O:21][C:19](=[O:20])[CH2:18]1>O>[CH:7]([N:6]([C:19](=[O:20])[CH2:18][C:17]([CH3:16])=[O:21])[C:5]1[CH:10]=[CH:11][C:2]([Cl:1])=[CH:3][CH:4]=1)([CH3:9])[CH3:8]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 12661DiketeneHCID 698644-Chloro-N-isopropylaniline

Product 1

HCID 20297524N-isopropyl-4'-chloroacetoacetanilide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 500 ml reaction flask fitted with a condenser, drying tube, magnetic stirrer and therometer was charged with 89.5 g (0.528 mole) of 4-chloro-N-isopropylaniline, 200 ml of glacial acetic acid and 18.5 g (0.58 mole) of mercuric acetate. To the stirred solution there was added dropwise 48.8 g (0.58 mole) of diketene while the reaction temperature was maintained at 30°-5°. The reaction solution was allowed to stir overnight at ambient temperature. The solution was mixed with two liters of water and twice extracted with ether. The organic phase was washed with water and dried over sodium sulfate. After removing the solvent, the liquid residue weighed 134 g (100%). N.M.R. (CDCl3) ∂1.0 and 1.2 (isopropyl, doublet), 1.8 (CH3, enol), 2.1 (CH3, keto), 3.2 (CH2), 4.7-5.2 (CH, isopropyl), 7.1-7.5 (aromatic).

Workup

  1. customA 500 ml reaction flask
  2. customfitted with a condenser
  3. customdrying tube, magnetic stirrer
  4. temperaturewas maintained at 30°-5°
  5. extractiontwice extracted with ether
  6. washThe organic phase was washed with water
  7. dry with materialdried over sodium sulfate
  8. customAfter removing the solvent

Sources & evidence

ORD record
ord-44263166478a440c88dfc227f53d23fa
Source dataset
uspto-grants-1980_11
Patent number
US04232163

Reaction notes

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