HCID 14722316, compound → HCID 14722448, compound

HRID 1031711Notes

Reaction equation

HRID 1031711 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[CH:7]=[C:8]([CH:16]=[CH:17][C:18]=1[O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[O:9][CH:10]([CH3:15])[CH2:11][C:12]([OH:14])=O)(=[O:4])=[O:3]>C(OCC)(=O)C>[CH3:15][CH:10]1[CH2:11][C:12](=[O:14])[C:16]2[CH:17]=[C:18]([O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:6]([NH:5][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:7][C:8]=2[O:9]1

Participants

3

Reactant 1

HCID 14722316HCID 14722316, compound

Product 1

HCID 14722448HCID 14722448, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

100 g of polyphosphoric acid was added to 5.69 g of 3-(3-methylsulfonylamino-4-phenoxyphenoxy)-3-methylpropionic acid. The mixture was stirred for 1 hour at 65° C. The reaction mixture was introduced into 400 ml of ice water, and 150 ml of ethyl acetate was added thereto. The organic layer was separated and the solvent was removed by distillation under reduced pressure. The residue was dissolved in 150 ml of 1N aqueous sodium hydroxide solution. The solution was washed with diethyl ether and adjusted to pH 4 with 4N hydrochloric acid. 150 ml of ethyl acetate was 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 purified by a column chromatography (eluant: a 25:1 mixture of toluene and ethyl acetate) and recrystallized from ethanol to obtain 2.16 g (yield: 40%) of 2,3-dihydro-2-methyl-7-methylsulfonylamino-6-phenoxy-4H-1-benzopyran-4-one

Workup

  1. additionwas added
  2. customThe organic layer was separated
  3. customthe solvent was removed by distillation under reduced pressure
  4. dissolutionThe residue was dissolved in 150 ml of 1N aqueous sodium hydroxide solution
  5. washThe solution was washed with diethyl ether
  6. addition150 ml of ethyl acetate was added
  7. customThe organic layer was separated
  8. washwashed with water
  9. dry with materiala saturated aqueous sodium chloride solution in this order, and dried with anhydrous magnesium sulfate
  10. customThe solvent was removed by distillation under reduced pressure
  11. customThe residue was purified by a column chromatography (eluant
  12. additiona 25:1 mixture of toluene and ethyl acetate) and
  13. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-f2610c93b62849b6b14ccec96ad9a1e9
Source dataset
uspto-grants-1990_09
Patent number
US04954518

Reaction notes

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