3-Ethoxycarbonyl-2-methylsulfinyl-4-oxo-4H-1-benzothiopyran → HCID 178418626, compound

HRID 5355Notes

Reaction equation

HRID 5355 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:11](=[O:12])[C:10]2[CH:13]=[CH:14][CH:15]=[CH:16][C:9]=2[S:8][C:7]=1[S:17](C)=O)=[O:5])[CH3:2].S.[Na]>O1CCCC1>[CH2:1]([O:3][C:4]([C:6]1[C:11](=[O:12])[C:10]2[CH:13]=[CH:14][CH:15]=[CH:16][C:9]=2[S:8][C:7]=1[SH:17])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 197957593-Ethoxycarbonyl-2-methylsulfinyl-4-oxo-4H-1-benzothiopyranHCID 86586439Sodium hydrogen sulphide

Product 1

HCID 178418626HCID 178418626, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 100 mg (0.337 mmol) of the compound of Example 18 in 1.8 ml of tetrahydrofuran was added 1N sodium hydrogensulfide (0.697 mmol), and the mixture was stirred for 3 hours. Solvent was distilled off and 87 mg of sodium bicarbonate and 6.5 ml of water were added to the residue, which was washed with dichloromethane. After added 2.2 ml of 1N hydrochloric acid, this was extracted with dichloromethane. The organic layer was washed with saturated saline solution and concentrated. The residue was purified by means of silica gel column chromatography (CHCl3) to obtain title compound (yield 23%).

Workup

  1. distillationSolvent was distilled off
  2. addition87 mg of sodium bicarbonate and 6.5 ml of water were added to the residue, which
  3. washwas washed with dichloromethane
  4. additionAfter added 2.2 ml of 1N hydrochloric acid
  5. extractionthis was extracted with dichloromethane
  6. washThe organic layer was washed with saturated saline solution
  7. concentrationconcentrated
  8. customThe residue was purified by means of silica gel column chromatography (CHCl3)

Sources & evidence

ORD record
ord-e4a23dd9d11840d1854afd3d74c6084e
Source dataset
uspto-grants-1993_09
Patent number
US05244892

Reaction notes

Loading…