Acetic Anhydride → HCID 21914847, compound

HRID 1246478Notes

Reaction equation

HRID 1246478 reaction equation
[CH3:1][S:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.[C:11]([NH:14][CH2:15][C:16]([OH:18])=[O:17])(=O)[CH3:12].C(OC(=O)C)(=O)C.C([O-])(=O)C.[Na+]>C(OCC)(=O)C>[CH3:12][C:11]1[O:18][C:16](=[O:17])/[C:15](=[CH:7]/[C:6]2[CH:9]=[CH:10][C:3]([S:2][CH3:1])=[CH:4][CH:5]=2)/[N:14]=1

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 10972AcetylglycineHCID 769854-(Methylthio)benzaldehydeHCID 517045Sodium Acetate

Product 1

HCID 21914847HCID 21914847, compoundYield 36.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-(Methylsulfanyl)benzaldehyde (31.8 g), (acetylamino)acetic acid (24.5 g) and acetic anhydride (35 ml) were combined, and then sodium acetate (8.57 g) was added to the suspension at room temperature under nitrogen atmosphere. The reaction mixture was refluxed for 3.5 hours. After cooled to room temperature, the mixture was poured into ice-water and ethyl acetate with stirring, and filtered in vacuo. The filtrate was separated. The organic layer was washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated in vacuo. The residue and the previously obtained solid were combined, and the mixture was purified by flash column chromatography over silica gel with chloroform/ethyl acetate (30:1) as an eluent, and triturated with isopropyl ether to give (4Z)-2-methyl-4-(4-(methylsulfanyl)benzylidene)-1,3-oxazol-5(4H)-one (17.8 g) as a brown solid.

Workup

  1. temperatureThe reaction mixture was refluxed for 3.5 hours
  2. filtrationfiltered in vacuo
  3. customThe filtrate was separated
  4. washThe organic layer was washed with saturated sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customthe mixture was purified by flash column chromatography over silica gel with chloroform/ethyl acetate (30:1) as an eluent
  8. customtriturated with isopropyl ether

Sources & evidence

ORD record
ord-8fb485a4f9cc486dabb4aaa4c8b394b3
Source dataset
uspto-grants-2006_10
Patent number
US07125901B2

Reaction notes

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