Acetic Anhydride → HCID 12669250, compound

HRID 430508

Reaction equation

HRID 430508 reaction equation
[C:1]([NH:4][C:5]1[CH:9]=[CH:8][S:7][C:6]=1[C:10]([OH:12])=[O:11])(=O)[CH3:2].C([O-])(=O)C.[Na+].C(OC(=O)C)(=O)C>O1CCOCC1>[CH3:2][C:1]1[O:12][C:10](=[O:11])[C:6]2[S:7][CH:8]=[CH:9][C:5]=2[N:4]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 517045Sodium AcetateHCID 28075793-Acetamidothiophene-2-carboxylic acid

Product 1

HCID 12669250HCID 12669250, compoundYield 119.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a mixture of 3-acetamidothiophene-2-carboxylic acid (15.1 g, 75.67 mmol) and sodium acetate (6.45 g, 78.6 mmol) in dioxane (200 mL) was added acetic anhydride (71 mL, 75.7 mmol). The reaction was refluxed 2 hours, cooled to ambient temperature and partitioned between chloroform and water. Phases were separated and the aqueous layer was extracted with chloroform. The combined organic phase was washed with water and brine, dried over magnesiuym sulfate and concentrated to leave 15.1 g of 2-methyl-thieno[3,2-d][1,3]oxazin-4-one as a brown oil which slowly solidified.

Workup

  1. temperatureThe reaction was refluxed 2 hours
  2. custompartitioned between chloroform and water
  3. customPhases were separated
  4. extractionthe aqueous layer was extracted with chloroform
  5. washThe combined organic phase was washed with water and brine
  6. dry with materialdried over magnesiuym sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-82c2df153c004ea5b5d5c17398b9629d
Source dataset
uspto-grants-2001_11
Patent number
US06323208B1

Linked notes

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