Water → 2-(2-Bromoethyl)-6-chloro-3,4-dihydro-4-hydroxy-2H-thieno[3,2-e]-1,2-thiazine 1,1-dioxide

HRID 1736000Notes

Reaction equation

HRID 1736000 reaction equation
[Cl:1][C:2]1[S:10][C:9]2[S:8](=[O:12])(=[O:11])[NH:7][CH2:6][CH:5]([OH:13])[C:4]=2[CH:3]=1.[H-].[Na+].[Br:16][CH2:17][CH2:18]Br.O>CN(C=O)C>[Br:16][CH2:17][CH2:18][N:7]1[CH2:6][CH:5]([OH:13])[C:4]2[CH:3]=[C:2]([Cl:1])[S:10][C:9]=2[S:8]1(=[O:11])=[O:12]

Participants

6

Reactant 4

HCID 962WaterHCID 78391,2-DibromoethaneHCID 24758Sodium hydrideHCID 110100596-Chloro-4-hydroxy-3,4-dihydro-2H-thieno[3,2-e][1,2]thiazine 1,1-dioxide

Product 1

HCID 194340152-(2-Bromoethyl)-6-chloro-3,4-dihydro-4-hydroxy-2H-thieno[3,2-e]-1,2-thiazine 1,1-dioxideYield 53%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-chloro-3,4-dihydro-4-hydroxy-2H-thieno[3,2-e]-1,2-thiazine 1,1-dioxide (2.0 g, 8.37 mmol) in DMF (50 mL) was added sodium hydride (0.37 g, 9.2 mmol), after stirring for 30 min 1,2-dibromoethane (2.36 g, 16.7 mmol) was added and this mixture was stirred at room temperature for 72 hr. The reaction mixture was poured into water and the aqueous mixture was extracted with ether. The combined extracts were dried (MgSO4) and evaporated to an oil which was purified by column chromatography (silica, 30% ethyl acetate/hexane) to give 1.52 g (53%) of the desired product as a viscous syrup which was used in the next step.

Workup

  1. additionwas added
  2. extractionthe aqueous mixture was extracted with ether
  3. dry with materialThe combined extracts were dried (MgSO4)
  4. customevaporated to an oil which
  5. customwas purified by column chromatography (silica, 30% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-f3251b234e1d4e36b80758ce0710c2f9
Source dataset
uspto-grants-1996_07
Patent number
US05538966

Reaction notes

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