Acetone → Acetanilide

HRID 1381195Notes

Reaction equation

HRID 1381195 reaction equation
C(=O)([O-])[O-].[K+].[K+].COC([C:11]1[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=1[NH2:13])=O.[CH3:18][C:19](C)=[O:20].COC1C=C(C=CC=1OC)C(N1CCN(CC(Cl)=O)CC1)=O>O.CC(C)=O>[C:19]([NH:13][C:12]1[CH:11]=[CH:17][CH:16]=[CH:15][CH:14]=1)(=[O:20])[CH3:18]

Participants

6

Reactant 4

HCID 180AcetoneHCID 8635Methyl AnthranilateHCID 11430Potassium CarbonateHCID 23323533[4-(3,4-Dimethoxybenzoyl)-1-piperazinyl]acetyl chloride

Product 1

HCID 904Acetanilide

Reagents, catalysts & solvents 1

HCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

8.28 Grams of potassium carbonate was dissolved in 50 ml of water-acetone (1:2), and to this solution was added 15.1 g of o-methoxycarbonylaniline. Under ice-cooled condition, an acetone solution of 34.4 g of [4-(3,4-dimethoxybenzoyl)-1-piperazinyl]acetylchloride was added dropwise thereto. After completion of the addition, the reaction was carried out at a room temperature for 3 hours, then acetone was removed by distillation. The residue obtained was extracted with chloroform, then the extract was washed with water, dried and chloroform was removed by distillation. The residue obtained was crystallized by adding ethyl acetate, and the crystals were collected by filtration. Recrystallized from ethanol to obtain 29 g o-methoxycarbonyl-α-[4-3,4-dimethoxybenzoyl)-1-piperazinyl]acetanilide in the form of colorless needle-like crystals. Melting point: 167.5°-169.0° C.

Workup

  1. temperatureUnder ice-cooled condition
  2. additionAfter completion of the addition
  3. customacetone was removed by distillation
  4. customThe residue obtained
  5. extractionwas extracted with chloroform
  6. washthe extract was washed with water
  7. customdried
  8. customchloroform was removed by distillation
  9. customThe residue obtained
  10. customwas crystallized
  11. additionby adding ethyl acetate
  12. filtrationthe crystals were collected by filtration
  13. customRecrystallized from ethanol

Sources & evidence

ORD record
ord-f0797784d47b4f8a9500af4d742d99bb
Source dataset
uspto-grants-1986_04
Patent number
US04585774

Reaction notes

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