Sodium Chloride → HCID 18654596, compound

HRID 2225475Notes

Reaction equation

HRID 2225475 reaction equation
[Cl:1][C:2]1[S:10][C:9]2[S:8](=[O:12])(=[O:11])[NH:7][CH2:6][C@@H:5]([OH:13])[C:4]=2[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:21][CH2:22][CH2:23][CH2:24][O:25][CH3:26].[Cl-].[Na+]>CS(C)=O>[Cl:1][C:2]1[S:10][C:9]2[S:8](=[O:11])(=[O:12])[N:7]([CH2:21][CH2:22][CH2:23][CH2:24][O:25][CH3:26])[CH2:6][C@@H:5]([OH:13])[C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 11430Potassium CarbonateHCID 5211681-Bromo-4-methoxybutane3×HCID 11746721(4S)-6-chloro-1,1-dioxo-3,4-dihydro-2H-thieno(3,2-e)thiazin-4-ol

Product 1

HCID 18654596HCID 18654596, compoundYield 204.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of (S)-3,4-dihydro-6-chloro-4-hydroxy-2H-thieno[3,2-e]-1,2-thiazine-1,1-dioxide (5, 65.4 g) and potassium carbonate (113.3 g) in dimethylsulfoxide (350 mL) was treated with 1-bromo-4-methoxybutane (20.6 g) and the mixture was stirred at ambient temperature for 4 hours. Another 20.6 grams of 1-bromo-4-methoxybutane was then added and the mixture was stirred at ambient temperature for 18 hours. TLC analysis after this period indicated incomplete reaction, so another 4.6 grams of 1-bromo-4methoxybutane was added and the mixture was stirred at ambient temperature for another 3 hours. At this point, TLC indicated complete reaction. The mixture was poured into saturated aqueous sodium chloride (1 L) and extracted with diethyl ether (3×150 mL). The organic phase was washed sequentially with 100 mL each of 10% aqueous sodium hydroxide, 1:1 5.25% sodium hypochlorite/water, and saturated aqueous sodium chloride, dried over sodium sulfate, and stripped of solvent by rotary evaporation. Residual solvent was removed under vacuum to provide 82 grams (92%) of (S)-3,4-dihydro-6-chloro-4-hydroxy-2-(4-methoxybutyl)-2H-thieno[3,2-e]-1,2-thiazine-1,1-dioxide as a light yellow oil: IR (film) 3500, 3350, 3070, 2950, 2850, 1525, 1480, 1440, 1380, 1330, 1160, 1120, 1080, 1020, 1100 cm-1 ; [α]25D +11.4° (c=1.1, methanol); Anal. Calcd for C11H16ClNO4S2 : C, 40.55; H, 4.95; N, 4.30. Found: C, 40.47; H, 4.99; N, 4.27.

Workup

  1. stirringthe mixture was stirred at ambient temperature for 18 hours
  2. waitTLC analysis after this period indicated incomplete
  3. customreaction
  4. stirringthe mixture was stirred at ambient temperature for another 3 hours
  5. customreaction
  6. extractionextracted with diethyl ether (3×150 mL)
  7. washThe organic phase was washed sequentially with 100 mL each of 10% aqueous sodium hydroxide, 1:1 5.25% sodium hypochlorite/water, and saturated aqueous sodium chloride
  8. dry with materialdried over sodium sulfate
  9. customstripped of solvent by rotary evaporation
  10. customResidual solvent was removed under vacuum

Sources & evidence

ORD record
ord-dd52170b02bb438c9e905508254677e6
Source dataset
uspto-grants-1994_09
Patent number
US05344929

Reaction notes

Loading…