Acetanilide → HCID 131714647, compound

HRID 1381203Notes

Reaction equation

HRID 1381203 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[H-].[Na+].CI.[C:15]([O-:20])(=[O:19])[C:16]([O-:18])=[O:17]>CN(C)C=O>[C:15]([OH:20])(=[O:19])[C:16]([OH:18])=[O:17].[C:15]([OH:20])(=[O:19])[C:16]([OH:18])=[O:17].[C:1]([NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 904AcetanilideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 71081Oxalate

Product 1

HCID 131714647HCID 131714647, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5 Grams of o-methoxycarbonyl- -[4-3,4-dimethoxybenzoyl)-1-piperazinyl]acetanilide was suspended in 50 ml of dimethylformamide, then 621 mg of 50% oily sodium hydride was added to the suspension and stirred at a room temperature for 1 hour. Next, under ice-cooled condition, 2.5 g of methyl iodide was added dropwise to the suspention and stirred at a room temperature for 4 hours. The solvent was removed by distillation under a reduced pressure, the residue obtained was extracted with chloroform and 1N-sodium hydroxide aqueous solution. The chloroform layer was washed with water, dried and then chloroform was removed by distillation. The residue obtained was purified by a silica gel column chromatography, and the product obtained was converted into an oxalate, recrystallized from methanol-ether to obtain 3.11 g of o-methoxy-carbonyl-N-methyl-α-[4-dimethoxy-benzoyl)-1-piperazinyl]-acetanilide dioxalate in the form of colorless powdery crystals. Melting point: 181.0°-182.0° C. (decomposed).

Workup

  1. additionwas added dropwise to the suspention
  2. stirringstirred at a room temperature for 4 hours
  3. customThe solvent was removed by distillation under a reduced pressure
  4. customthe residue obtained
  5. extractionwas extracted with chloroform and 1N-sodium hydroxide aqueous solution
  6. washThe chloroform layer was washed with water
  7. customdried
  8. customchloroform was removed by distillation
  9. customThe residue obtained
  10. customwas purified by a silica gel column chromatography
  11. customthe product obtained
  12. customrecrystallized from methanol-ether

Sources & evidence

ORD record
ord-c09f5c2025c643f594dd55f557bbf0e7
Source dataset
uspto-grants-1986_04
Patent number
US04585774

Reaction notes

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