Sodium Iodide → HCID 21712802, compound

HRID 2289437Notes

Reaction equation

HRID 2289437 reaction equation
[OH-].[K+].[CH3:3][O:4][C:5]([C:7]1[S:16][C:10]2[S:11][CH2:12][C:13](=[O:15])[NH:14][C:9]=2[CH:8]=1)=[O:6].[I-].[Na+].[CH3:19][S:20][CH2:21][CH2:22]Cl>CS(C)=O.O>[CH3:3][O:4][C:5]([C:7]1[S:16][C:10]2[S:11][CH2:12][C:13](=[O:15])[N:14]([CH2:22][CH2:21][S:20][CH3:19])[C:9]=2[CH:8]=1)=[O:6]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 109652-Chloroethyl methyl sulfideHCID 14797Potassium HydroxideHCID 15501266HCID 15501266, compound

Product 1

HCID 21712802HCID 21712802, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

Under nitrogen atmosphere, potassium hydroxide (147 mg) in dimethyl sulfoxide (10 ml) was stirred at room temperature for 30 minutes. To the solution were added 2,3-dihydro-6-methoxycarbonyl-2-oxothieno[2,3-b][1,4]thiazine (0.50 g), sodium iodide (0.39 g) and 2-chloroethyl methyl sulfide (0.26 ml), and the mixture was stirred at 50° C. for 6.5 hours. The mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: hexane:ethyl acetate=3:1) to give 2,3-dihydro-6-methoxycarbonyl-1-(2-(methylthio)-ethyl]-2-oxothieno[2,3-b][1,4]thiazine (463 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (eluent: hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-5dbc68512f334c95b7a4115b8a65f31e
Source dataset
uspto-grants-2000_07
Patent number
US06093710

Reaction notes

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