Acetic Anhydride → HCID 15425486, compound

HRID 430520Notes

Reaction equation

HRID 430520 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-5af439811b79488f89d0fae366e95abb
Source dataset
uspto-grants-2001_11
Patent number
US06323208B1

Reaction notes

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