Acetic Anhydride → 4-[(3,4-Diethoxyphenyl)methylene]-2-methyl-5(4H)-oxazolone

HRID 1739437Notes

Reaction equation

HRID 1739437 reaction equation
C(OC(=O)C)(=O)C.[CH2:8]([O:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][C:18]=1[O:19][CH2:20][CH3:21])[CH:14]=O)[CH3:9].[C:22]([NH:25][CH2:26][C:27]([OH:29])=[O:28])(=O)[CH3:23].C([O-])(=O)C.[Na+]>O>[CH2:8]([O:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][C:18]=1[O:19][CH2:20][CH3:21])[CH:14]=[C:26]1[C:27](=[O:28])[O:29][C:22]([CH3:23])=[N:25]1)[CH3:9]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 10972AcetylglycineHCID 748473,4-DiethoxybenzaldehydeHCID 517045Sodium Acetate

Product 1

HCID 544335354-[(3,4-Diethoxyphenyl)methylene]-2-methyl-5(4H)-oxazoloneYield 45%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To acetic anhydride (193 ml) are added 3,4-diethoxybenzaldehyde (234.4 g), N-acetylglycine (95.4 g) and sodium acetate (49.5 g), and the mixture is heated under reflux for one hour, and the reaction mixture is allowed to stand for cooling. The reaction mixture is further allowed to stand in a refrigerator overnight, and then thereto is added water. The mixture is extracted with chloroform, and the extract is washed, dried and concentrated. The residue is crystallized from ethanol to give 4-(3,4-diethoxybenzylidene)-2-methyloxazol-5(4H)-one (100.9 g).

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for one hour
  3. temperaturefor cooling
  4. customto stand in a refrigerator overnight
  5. extractionThe mixture is extracted with chloroform
  6. washthe extract is washed
  7. customdried
  8. concentrationconcentrated
  9. customThe residue is crystallized from ethanol

Sources & evidence

ORD record
ord-9f5164a76cf441b7a949db897de885d5
Source dataset
uspto-grants-1999_10
Patent number
US05965730

Reaction notes

Loading…