Acetic Anhydride → HCID 11791785, compound

HRID 1031676Notes

Reaction equation

HRID 1031676 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])[C:5]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:4][C:3]=1[C:20]([CH3:22])=[O:21].[C:23](OC(=O)C)(=O)[CH3:24].C([O-])(=O)C.[Na+].C(OCC)(=O)C>O>[CH3:23][C:24]1[O:1][C:2]2[CH:7]=[C:6]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])[C:5]([O:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:4][C:3]=2[C:20](=[O:21])[CH:22]=1

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 8857Ethyl AcetateHCID 517045Sodium AcetateHCID 10734538HCID 10734538, compound

Product 1

HCID 11791785HCID 11791785, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

There were mixed 3.21 g of methyl 2-hydroxy-4-methylsulfonylamino-5-phenoxyphenyl ketone, 5.45 g of acetic anhydride and 4.1 g of sodium acetate. The mixture was stirred for 1.5 hours at 130°-140° C. The reaction mixture was cooled to room temperature. 200 ml of ethyl acetate and 100 ml of water were added thereto. The organic layer was separated, washed with water and a saturated aqueous sodium chloride solution in this order, and dried with anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was recrystallized from ethyl acetate-diisopropyl ether to obtain 860 mg (yield: 25%) of 2-methyl-7-methylsulfonylamino-6-phenoxy-4H-1-benzopyran-4-one having a melting point of 186.5°-187° C.

Workup

  1. customThe organic layer was separated
  2. washwashed with water
  3. dry with materiala saturated aqueous sodium chloride solution in this order, and dried with anhydrous magnesium sulfate
  4. customThe solvent was removed by distillation under reduced pressure
  5. customThe residue was recrystallized from ethyl acetate-diisopropyl ether

Sources & evidence

ORD record
ord-d4db2f62ba7e48ef9c296a25146fc755
Source dataset
uspto-grants-1990_09
Patent number
US04954518

Reaction notes

Loading…