Ethanol → 5,6-Dihydro-4H-thieno[2,3-b]thiopyran-2-sulfonamide 7,7-dioxide

HRID 653456Notes

Reaction equation

HRID 653456 reaction equation
[S:1]1[C:5]2[S:6](=[O:11])(=[O:10])[CH2:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[S:12]([NH2:15])(=[O:14])=[O:13].C(O)C>[Pd].CO>[S:1]1[C:5]2[S:6](=[O:10])(=[O:11])[CH2:7][CH2:8][CH2:9][C:4]=2[CH:3]=[C:2]1[S:12]([NH2:15])(=[O:13])=[O:14]

Participants

5

Reactant 2

HCID 702EthanolHCID 137631516H-Thieno[2,3-b]thiopyran-2-sulfonamide-7,7-dioxide

Product 1

HCID 137631525,6-Dihydro-4H-thieno[2,3-b]thiopyran-2-sulfonamide 7,7-dioxideYield 76%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 887MethanolSolvent

Procedure

A solution of 6H-thieno[2,3-b]thiopyran-2-sulfonamide-7,7-dioxide (3.05 g, 0.011 m) is absolute ethanol (130 ml) and methanol (20 ml) was hydrogenated on a Parr apparatus at 40 psi with 5% palladium on carbon catalyst (250 mg) at ambient temperature. After 15 minutes, 10% palladium on carbon catalyst (350 mg) was added, followed by an identical addition after 30 minutes. After 16 hours, the catalyst was filtered and the filtrate was concentrated in vacuo. The residue was dissolved in absolute ethanol (100 ml) and methanol (50 ml) and hydrogenated at 50 psi with 10% palladium on carbon catalyst (500 mg) for 16 hours. The catalyst was filtered off and the filtrate was evaporated under reduced pressure. The solid residue was chromatographed on silica gel, eluting with 10% methanol-chloroform to give 2.33 g (76%) of product.

Workup

  1. additionfollowed by an identical addition after 30 minutes
  2. waitAfter 16 hours
  3. filtrationthe catalyst was filtered
  4. concentrationthe filtrate was concentrated in vacuo
  5. dissolutionThe residue was dissolved in absolute ethanol (100 ml)
  6. waitmethanol (50 ml) and hydrogenated at 50 psi with 10% palladium on carbon catalyst (500 mg) for 16 hours
  7. filtrationThe catalyst was filtered off
  8. customthe filtrate was evaporated under reduced pressure
  9. customThe solid residue was chromatographed on silica gel
  10. washeluting with 10% methanol-chloroform

Sources & evidence

ORD record
ord-23d3e60719b6404c96bb8e7227cfccff
Source dataset
uspto-grants-1987_06
Patent number
US04677115

Reaction notes

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