Water → HCID 14722438, compound

HRID 1031692Notes

Reaction equation

HRID 1031692 reaction equation
C([NH:4][C:5]1[C:15]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:14][C:8]2[C:9](=[O:13])[CH:10]=[CH:11][O:12][C:7]=2[CH:6]=1)(=O)C.CC(C)([O-])C.[K+].[CH2:29]([S:31](Cl)(=[O:33])=[O:32])[CH3:30].O>CN(C)C=O.C(OCC)(=O)C>[CH2:29]([S:31]([NH:4][C:5]1[C:15]([O:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[CH:14][C:8]2[C:9](=[O:13])[CH:10]=[CH:11][O:12][C:7]=2[CH:6]=1)(=[O:33])=[O:32])[CH3:30]

Participants

7

Reactant 4

HCID 962WaterHCID 11667Ethanesulfonyl chlorideHCID 22168210HCID 22168210, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 14722438HCID 14722438, compoundYield 21.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2.95 g of 7-acetylamino-6-phenoxy-4H-1-benzopyran-4-one was dissolved in 30 ml of N,N-dimethylformamide. 1.35 g of potassium tert-butoxide was added with ice-cooling. The mixture was stirred for 30 minutes at the same temperature. Then, 1.55 g of ethanesulfonyl chloride was added thereto dropwise. The mixture was stirred for 1 hour at 20°-25° C. 200 ml of water and 200 ml of ethyl acetate were added. The organic layer was separated. The solvent was removed by distillation under reduced pressure. The resulting crystal was mixed with 20 ml of a 1N aqueous sodium hydroxide solution and 10 ml of ethanol. The mixture was refluxed for 2 hours. 100 ml of water and 100 ml of ethyl acetate were added thereto. The mixture was adjusted to pH 4 with 4N hydrochloric acid. The organic layer was separated. The layer was washed with water and a saturated aqueous NaCl solution in this order, 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 mixture of 5:1 toluene and ethyl acetate) to obtain 0.75 g (yield: 21.7%) of 7-ethylsulfonylamino-6-phenoxy-4H-1-benzopyran-4-one.

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred for 1 hour at 20°-25° C
  3. customThe organic layer was separated
  4. customThe solvent was removed by distillation under reduced pressure
  5. additionThe resulting crystal was mixed with 20 ml of a 1N aqueous sodium hydroxide solution and 10 ml of ethanol
  6. temperatureThe mixture was refluxed for 2 hours
  7. addition100 ml of water and 100 ml of ethyl acetate were added
  8. customThe organic layer was separated
  9. washThe layer was washed with water
  10. dry with materiala saturated aqueous NaCl solution in this order, and dried with anhydrous magnesium sulfate
  11. customThe solvent was removed by distillation under reduced pressure
  12. customThe residue was purified by a column chromatography (eluant
  13. additiona mixture of 5:1 toluene and ethyl acetate)

Sources & evidence

ORD record
ord-cef33f1899de44cda3c3d6160fb06a31
Source dataset
uspto-grants-1990_09
Patent number
US04954518

Reaction notes

Loading…