N-(4-Methoxyphenyl)Acetamide → HCID 18606094, compound

HRID 1382361Notes

Reaction equation

HRID 1382361 reaction equation
[CH3:1][C:2]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1)=[O:3].[H-].[Na+].Br[CH:16]([CH3:22])[C:17]([O:19]CC)=[O:18]>C1(C)C=CC=CC=1>[C:2]([N:4]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1)[C@H:16]([C:17]([OH:19])=[O:18])[CH3:22])(=[O:3])[CH3:1]

Participants

5

Reactant 3

HCID 5827N-(4-Methoxyphenyl)AcetamideHCID 24758Sodium hydrideHCID 79040Ethyl 2-bromopropionate

Product 1

HCID 18606094HCID 18606094, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mechanically stirred solution of dry 4-methoxyacetanilide (0.25 mol) in anhydrous toluene (500 mL) was treated with NaH (57% oil dispersion, 11.57 g, 0.28 mol) and heated under reflux for 2 h (hours). Ethyl 2-bromopropionate (37.5 mL, 0.29 mol) was added and the mixture was refluxed for 2 h. The cooled mixture was centrifuged to facilitate separation of the NaBr and filtered, and the toluene solution was evaporated to dryness in vacuo. The syrupy residue was dissolved in ethanol (300 mL), a solution of NaOH (20 g) in water (30 mL) was added, and the mixture was heated under reflux for 1 h. The cooled solution was concentrated in vacuo, water (700 mL) was added, and the mixture was extracted with CH2Cl2 (2×200 mL). The mixture was acidified to pH 1 with concentrated HCl, the precipitate which formed was collected and crystallized from ethanol-water to give N-acetyl-N-(4-methoxyphenyl)alanine in 70% yield: mp (melting point) 197°-201° C.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 2 h (hours)
  3. temperaturethe mixture was refluxed for 2 h
  4. customseparation of the NaBr
  5. filtrationfiltered
  6. customthe toluene solution was evaporated to dryness in vacuo
  7. dissolutionThe syrupy residue was dissolved in ethanol (300 mL)
  8. additiona solution of NaOH (20 g) in water (30 mL) was added
  9. temperaturethe mixture was heated
  10. temperatureunder reflux for 1 h
  11. concentrationThe cooled solution was concentrated in vacuo, water (700 mL)
  12. additionwas added
  13. extractionthe mixture was extracted with CH2Cl2 (2×200 mL)
  14. customthe precipitate which formed
  15. customwas collected
  16. customcrystallized from ethanol-water

Sources & evidence

ORD record
ord-9afd4193ddc2483aadcfee5e2d3d118f
Source dataset
uspto-grants-1989_02
Patent number
US04806561

Reaction notes

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