Hydrochloric Acid → HCID 67826418, compound

HRID 1033085Notes

Reaction equation

HRID 1033085 reaction equation
C([NH:4][CH:5]1[CH2:10][CH:9]([CH2:11][CH2:12][CH2:13][O:14][CH3:15])[S:8](=[O:17])(=[O:16])[C:7]2[S:18][C:19]([S:21]([NH2:24])(=[O:23])=[O:22])=[CH:20][C:6]1=2)(=O)C.CO.[ClH:27].CCOCC>C(O)C>[ClH:27].[NH2:4][CH:5]1[CH2:10][CH:9]([CH2:11][CH2:12][CH2:13][O:14][CH3:15])[S:8](=[O:17])(=[O:16])[C:7]2[S:18][C:19]([S:21]([NH2:24])(=[O:23])=[O:22])=[CH:20][C:6]1=2

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 887MethanolHCID 3283Diethyl EtherHCID 67693194HCID 67693194, compound

Product 1

HCID 67826418HCID 67826418, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-acetamido-5,6-dihydro-6-(3-methoxypropyl)-4H-thieno[2,3-b]thiopyran-2-sulfonamide-7,7-dioxide (7.3 g), (prepared employing substantially the same procedures as described in Example 10, Steps A through I), methanol (70 ml.) and 6N HCl (70 ml.) was heated at reflux for 18 hours then evaporated at reduced pressure to a volume of 20 ml. The reaction mixture was made basic with aqueous NaHCO3 and extracted wth ethyl acetate (2×80 ml.). The organic phase was washed with brine, dried over Na2SO4 and evaporated in vacuo. The residue was crystallized from ethanol (20 ml.) to remove the cis isomer and the product thus obtained was redissolved in hot ethanol, treated with an excess of ethanolic HCl and ether to provide 1.0 g of the title compound which melts at 262° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 hours
  3. customthen evaporated at reduced pressure to a volume of 20 ml
  4. extractionextracted wth ethyl acetate (2×80 ml.)
  5. washThe organic phase was washed with brine
  6. dry with materialdried over Na2SO4
  7. customevaporated in vacuo
  8. customThe residue was crystallized from ethanol (20 ml.)
  9. customto remove the cis isomer
  10. customthe product thus obtained

Sources & evidence

ORD record
ord-dab1d4e790064cff92abe373716638ab
Source dataset
uspto-grants-1994_05
Patent number
US05308863

Reaction notes

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