Diethyl Ether → 7-methylsulfonylamino-6-phenoxy-4H-1-benzopyran-4-one

HRID 1031677Notes

Reaction equation

HRID 1031677 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].Cl(O)(=O)(=O)=O.[CH2:28](OCC)C>C([O-])([O-])OCC>[CH3:12][S:9]([NH:8][C:6]1[C:5]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:4][C:3]2[C:20](=[O:21])[CH:22]=[CH:28][O:1][C:2]=2[CH:7]=1)(=[O:11])=[O:10]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 24247Perchloric AcidHCID 10734538HCID 10734538, compound

Product 1

HCID 106164807-methylsulfonylamino-6-phenoxy-4H-1-benzopyran-4-oneYield 87.6%

Reagents, catalysts & solvents 1

HCID 53630039EthylorthoformateSolvent

Procedure

In 16 ml of ethyl orthoformate was suspended 3.21 g of methyl 2-hydroxy-4-methylsulfonylamino-5-phenoxyphenyl ketone. To the mixture being ice-cooled was dropwise added 2.15 g of a 70% aqueous perchloric acid solution in 10 minutes. Stirring was conducted for 30 minutes at 20°-25° C. 50 ml of diethyl ether was added thereto. The resulting crystal was collected by filtration. The crystal was mixed with 50 ml of water, and the mixture was refluxed for 2 minutes and then cooled to room temperature. The resulting crystal was collected by filtration and recrystallized from acetonitrile to obtain 2.90 g (yield: 87.6%) of 7-methylsulfonylamino-6-phenoxy-4H-1-benzopyran-4-one.

Workup

  1. temperaturecooled
  2. customin 10 minutes
  3. filtrationThe resulting crystal was collected by filtration
  4. additionThe crystal was mixed with 50 ml of water
  5. temperaturethe mixture was refluxed for 2 minutes
  6. filtrationThe resulting crystal was collected by filtration
  7. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-d8884ff329e045dd85b1d241225e4554
Source dataset
uspto-grants-1990_09
Patent number
US04954518

Reaction notes

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