Acetic Anhydride → HCID 14722436, compound

HRID 1031685Notes

Reaction equation

HRID 1031685 reaction equation
[C:1]([O:4][C:5](=O)[CH3:6])(=O)[CH3:2].[OH:8][C:9]1[CH:14]=[C:13]([NH:15][S:16]([CH3:19])(=[O:18])=[O:17])[C:12]([O:20][C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=2[F:28])=[CH:11][C:10]=1C(C)=O.C([O-])(=O)C.[Na+].C(OCC)(=O)C>O>[CH3:19][S:16]([NH:15][C:13]1[C:12]([O:20][C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=2[F:28])=[CH:11][C:10]2[C:9](=[O:8])[CH:14]=[C:5]([CH3:6])[O:4][C:1]=2[CH:2]=1)(=[O:17])=[O:18]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 8857Ethyl AcetateHCID 517045Sodium AcetateHCID 14722302HCID 14722302, compound

Product 1

HCID 14722436HCID 14722436, compoundYield 14.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.06 ml of acetic anhydride was added to 2.0 g of methyl 2-hydroxy-4-methylsulfonylamino-5-(2,4-difluorophenoxy)phenyl ketone and 550 mg of sodium acetate. The mixture was refluxed for 1 hour. The reaction mixture was introduced into a mixture of 50 ml of ethyl acetate and 50 ml of water. The organic layer was separated and washed with water. The solvent was removed by distillation under reduced pressure. The residue was dissolved in 20 ml of ethanol. 12 ml of a 1N aqueous sodium hydroxide solution was added thereto. The mixture was refluxed for 10 minutes. The reaction mixture was introduced into a mixture of 50 ml of ethyl acetate and 50 ml of water. The resulting mixture was adjusted to pH 2.0 with 4N hydrochloric acid. The organic layer was separated, washed with water, and dried with anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was purified by a column chromatography (eluant: a 10 : 1 mixture of toluene and ethyl acetate) to obtain 300 mg (yield: 14.4%) of 7-methylsulfonylamino-2-methyl-6-(2,4-difluorophenoxy)-4H-1-benzopyran-4-one.

Workup

  1. temperatureThe mixture was refluxed for 1 hour
  2. customThe organic layer was separated
  3. washwashed with water
  4. customThe solvent was removed by distillation under reduced pressure
  5. dissolutionThe residue was dissolved in 20 ml of ethanol
  6. addition12 ml of a 1N aqueous sodium hydroxide solution was added
  7. temperatureThe mixture was refluxed for 10 minutes
  8. additionThe reaction mixture was introduced into a mixture of 50 ml of ethyl acetate and 50 ml of water
  9. customThe organic layer was separated
  10. washwashed with water
  11. dry with materialdried with anhydrous magnesium sulfate
  12. customThe solvent was removed by distillation under reduced pressure
  13. customThe residue was purified by a column chromatography (eluant
  14. additiona 10 : 1 mixture of toluene and ethyl acetate)

Sources & evidence

ORD record
ord-d39816e53f504d48ab7566574afcf227
Source dataset
uspto-grants-1990_09
Patent number
US04954518

Reaction notes

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