Dimethyl Sulfide → HCID 67692829, compound

HRID 1033080Notes

Reaction equation

HRID 1033080 reaction equation
[C:1]([NH:4][CH:5]1[CH2:10][CH:9]([CH2:11][CH2:12][O:13][CH2:14][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)[CH3:2].B.CSC.CSC>O1CCCC1>[CH2:14]([O:13][CH2:12][CH2:11][CH:9]1[S:8](=[O:16])(=[O:17])[C:7]2[S:18][C:19]([S:21]([NH2:24])(=[O:23])=[O:22])=[CH:20][C:6]=2[CH:5]([NH:4][CH2:1][CH3:2])[CH2:10]1)[CH3:15]

Participants

5

Reactant 3

HCID 1068Dimethyl SulfideHCID 12423031(Dimethyl sulfide)trihydroboronHCID 67694362HCID 67694362, compound

Product 1

HCID 67692829HCID 67692829, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 4-acetamido-5,6-dihydro-6-(2-ethoxyethyl)-4H-thieno[2,3-b]thiopyran-2-sulfonamide-7,7-dioxide (6.8 g, 0.017 mol) in tetrahydrofuran (20 ml) heated under nitrogen to reflux was added borane-methyl sulfide (17 ml, 0.170 mol) dropwise over 1/2 hr. The reaction was heated at reflux for 2 hr. while allowing the methyl sulfide to distill off. Then the mixture was concentrated in vacuo to a yellow gum. Then 6N HCl (30 ml) was added followed by water (30 ml) and the mixture was heated on the steam bath for 1/4 hour. The solution was basified with excess sodium bicarbonate and was extracted with ethyl acetate (300 ml). The aqueous solution was again extracted with ethyl acetate. The combined extracts were washed with saturated sodium chloride, dried, filtered and concentrated in vacuo to obtain a white foam (5.3 g) mixture of cis and trans isomers. Chromatography on silica gel gave 2.28 g of the a-isomer and 0.17 g of the β -isomer.

Workup

  1. temperatureto reflux
  2. temperatureThe reaction was heated
  3. temperatureat reflux for 2 hr
  4. distillationto distill off
  5. concentrationThen the mixture was concentrated in vacuo to a yellow gum
  6. additionThen 6N HCl (30 ml) was added
  7. temperaturethe mixture was heated on the steam bath for 1/4 hour
  8. extractionwas extracted with ethyl acetate (300 ml)
  9. extractionThe aqueous solution was again extracted with ethyl acetate
  10. washThe combined extracts were washed with saturated sodium chloride
  11. customdried
  12. filtrationfiltered
  13. concentrationconcentrated in vacuo
  14. customto obtain
  15. customChromatography on silica gel gave 2.28 g of the a-isomer and 0.17 g of the β -isomer

Sources & evidence

ORD record
ord-8f634deedd3d4eaab71c25d5f6b92262
Source dataset
uspto-grants-1994_05
Patent number
US05308863

Reaction notes

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