Acetic Anhydride → HCID 13092028, compound

HRID 647175Notes

Reaction equation

HRID 647175 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-a93235f75a394436bde4a94ed8a2332b
Source dataset
uspto-grants-1983_10
Patent number
US04407811

Reaction notes

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