Benzaldehyde → 4-Benzylidene-2-(2-chloro-phenyl)-4H-oxazol-5-one

HRID 44439Notes

Reaction equation

HRID 44439 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][CH:12]=[CH:11][C:3]=1[C:4]([NH:6][CH2:7][C:8]([OH:10])=[O:9])=O.C([O-])(=O)C.[Na+].C(OC(=O)C)(=O)C.[CH:27](=O)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>>[CH:27](=[C:7]1[C:8](=[O:10])[O:9][C:4]([C:3]2[CH:11]=[CH:12][CH:13]=[CH:14][C:2]=2[Cl:1])=[N:6]1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

5

Reactant 4

HCID 240BenzaldehydeHCID 7918Acetic AnhydrideHCID 177756Acetic acid, 2-((2-chlorobenzoyl)amino)-HCID 517045Sodium Acetate

Product 1

HCID 31092794-Benzylidene-2-(2-chloro-phenyl)-4H-oxazol-5-oneYield 90%

Conditions

Temperature
60 °C

Procedure

To the stirred mixture of (2-chloro-benzoylamino)-acetic acid 21 (23.41 mmol), anhydrous sodium acetate (70.23 mmol), acetic anhydride (7 ml), and benzaldehyde (25.75 mmol) were added dropwise at 30° C. This mixture was then heated to 60° C. for 1 hr. The reaction mixture was poured into an ice-water solution and the resulting solids were filtered, washed with ethanol and dried on vacuum. The desired compound was obtained with a 90% yield.

Workup

  1. additionwere added dropwise at 30° C
  2. filtrationthe resulting solids were filtered
  3. washwashed with ethanol
  4. customdried on vacuum

Sources & evidence

ORD record
ord-7272ad2e3b54445b9f9b585cd7162dd0
Source dataset
uspto-grants-2013_09
Patent number
US08541428B2

Reaction notes

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