Hydrochloric Acid → HCID 10621185, compound

HRID 1031684Notes

Reaction equation

HRID 1031684 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](OCC)(=O)[C:24]([O:26][CH2:27][CH3:28])=[O:25].[H-].[Na+].Cl>C(O)C>[CH2:27]([O:26][C:24]([C:23]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)=[O:25])[CH3:28]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7268Diethyl OxalateHCID 24758Sodium hydrideHCID 10734538HCID 10734538, compound

Product 1

HCID 10621185HCID 10621185, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

5.0 g of methyl 2-hydroxy-4-methylsulfonylamino-5-phenoxyphenyl ketone was suspended in 85 ml of ethanol. Thereto was added 4.5 ml of diethyl oxalate. Further, 3.1 g of sodium hydride (purity: 60%) was added thereto in portions in 10 minutes. The mixture was refluxed for 1.5 hours. The reaction mixture was introduced into 300 ml of ice water. The resulting mixture was adjusted to pH 2 with 4N hydrochloric acid. The resulting crystal was collected by filtration and then suspended in 50 ml of acetic acid. 1 ml of concentrated hydrochloric acid was added thereto. The mixture was stirred for 10 minutes at 80° C. After the completion of the reaction, 200 ml of water and 200 ml of ethyl acetate 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 a mixed solvent of ethyl acetate and diisopropyl ether to obtain 3.5 g (yield: 56%) of 2-ethoxycarbonyl-7-methylsulfonylamino-6-phenoxy-4H-1-benzopyran-4-one having a melting point of 155°-156° C.

Workup

  1. temperatureThe mixture was refluxed for 1.5 hours
  2. filtrationThe resulting crystal was collected by filtration
  3. addition1 ml of concentrated hydrochloric acid was added
  4. customAfter the completion of the reaction, 200 ml of water and 200 ml of ethyl acetate
  5. additionwere added
  6. customThe organic layer was separated
  7. washwashed with water
  8. dry with materiala saturated aqueous sodium chloride solution in this order, and dried with anhydrous magnesium sulfate
  9. customThe solvent was removed by distillation under reduced pressure
  10. customThe residue was recrystallized from a mixed solvent of ethyl acetate and diisopropyl ether

Sources & evidence

ORD record
ord-d587cde5dcda46258d8feef25b9c87da
Source dataset
uspto-grants-1990_09
Patent number
US04954518

Reaction notes

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