Acetic Anhydride → HCID 13092028, compound

HRID 434830Notes

Reaction equation

HRID 434830 reaction equation
Cl.[NH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]1[O:13][C:12](=[O:14])[NH:11][C:10]1=[O:15].[C:16]([O-])(=[O:18])[CH3:17].[Na+].C(OC(=O)C)(=O)C>C(O)(=O)C>[C:16]([NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]1[O:13][C:12](=[O:14])[NH:11][C:10]1=[O:15])(=[O:18])[CH3:17]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 517045Sodium AcetateHCID 13092027HCID 13092027, compound

Product 1

HCID 13092028HCID 13092028, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

5-(2-Aminophenyl)oxazolidine-2,4-dione hydrochloride (1 g., 4.37 mmoles) was taken into 15 ml. of glacial acetic acid. Sodium acetate (358 mg., 4.37 mmoles) was added and then, in a dropwise manner, acetic anhydride (449 mg., 0.41 ml., 4.37 mmoles). The reaction mixture was stirred at room temperature for 16 hours, poured into 50 ml. of water and extracted with three portions of ethyl acetate. The combined extracts were washed with two portions of water and then one of brine, dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo solids (0.72 g.). Recrystallization from ethyl acetate gave purified 5-(2-acetamidophenyl)oxazolidine-2,4-dione in two crops [0.26 g., m.p. 197°-198° C.; m/e 234].

Workup

  1. additionpoured into 50 ml
  2. extractionof water and extracted with three portions of ethyl acetate
  3. washThe combined extracts were washed with two portions of water
  4. dry with materialone of brine, dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo solids (0.72 g.)
  7. customRecrystallization from ethyl acetate
  8. customgave
  9. custompurified 5-(2-acetamidophenyl)oxazolidine-2,4-dione in two crops [0.26 g., m.p. 197°-198° C.; m/e 234]

Sources & evidence

ORD record
ord-f7b6b7b6d6a840d9aa575c0dfb67fa32
Source dataset
uspto-grants-1983_08
Patent number
US04399296

Reaction notes

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