Acetic Anhydride → HCID 13093538, compound

HRID 1163950Notes

Reaction equation

HRID 1163950 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[C:3]=1[CH:10]1[O:14][C:13](=[O:15])[NH:12][C:11]1=[O:16].[C:17](OC(=O)C)(=[O:19])[CH3:18]>O1CCCC1>[C:17]([N:12]1[C:11](=[O:16])[CH:10]([C:3]2[C:4]([O:8][CH3:9])=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])[O:14][C:13]1=[O:15])(=[O:19])[CH3:18]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 130920155-(2-Chloro-6-methoxyphenyl)-1,3-oxazolidine-2,4-dione

Product 1

HCID 13093538HCID 13093538, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-(2-Chloro-6-methoxyphenyl)oxazolidin-2,4-dione (1.21 g., 5 mmoles) was dissolved in 10 ml. of tetrahydrofuran. Acetic anhydride (613 mg. 0.57 ml. 6 mmoles) was added and the solution stirred at room temperature for 44 hours. The reaction mixture was concentrated to an oil, partitioned between chloroform and saturated sodium bicarbonate. The chloroform layer was washed with fresh bicarbonate and then brine, dried over anhydrous magnesium sulfate, filtered, and concentrated to solid. Repulp of the residue in about 50 ml. of ether gave 3-acetyl-5-(2-chloro-6-methoxyphenyl)oxazolidin-2,4-dione (790 mg., 56%; m.p. 132°-135° C. m/e 285/283).

Workup

  1. concentrationThe reaction mixture was concentrated to an oil
  2. custompartitioned between chloroform and saturated sodium bicarbonate
  3. washThe chloroform layer was washed with fresh bicarbonate
  4. dry with materialbrine, dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to solid

Sources & evidence

ORD record
ord-cf61406a8411463ab5ecd2fdfe6627c8
Source dataset
uspto-grants-1983_01
Patent number
US04367234

Reaction notes

Loading…