Acetic Anhydride → HCID 15425486, compound

HRID 1737265Notes

Reaction equation

HRID 1737265 reaction equation
[C:1]([NH:4][C:5]1[C:9]([C:10]([OH:12])=[O:11])=[CH:8][S:7][CH:6]=1)(=O)[CH3:2].C(OC(=O)C)(=O)C.C([O-])(=O)C.[Na+]>O1CCOCC1>[CH3:2][C:1]1[O:12][C:10](=[O:11])[C:9]2[C:5](=[CH:6][S:7][CH:8]=2)[N:4]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 517045Sodium AcetateHCID 18350683HCID 18350683, compound

Product 1

HCID 15425486HCID 15425486, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 3-acetamidothiophene-4-carboxylic acid (1.6 g, 8.65 mmol), dioxane (40 mL), acetic anhydride (10.2 mL, 86.5 mmol), and sodium acetate (0.75 g, 9.08 mmol) was refluxed overnight. The reaction was cooled and concentrated. The residue was partitioned between ethyl acetate and water. Phases were separated and the aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with water and brine, dried over sodium sulfate, and concentrated to afford 1.39 g (96%) of 2-methyl-thieno[3,4-d][1,3]oxazin-4-one as a tan solid.

Workup

  1. temperaturewas refluxed overnight
  2. temperatureThe reaction was cooled
  3. concentrationconcentrated
  4. customThe residue was partitioned between ethyl acetate and water
  5. customPhases were separated
  6. extractionthe aqueous layer was extracted with ethyl acetate
  7. washThe combined organic layer was washed with water and brine
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-a55d8756df0a466a9578cd028ebaa75f
Source dataset
uspto-grants-1999_10
Patent number
US05962457

Reaction notes

Loading…