Allyl bromide → HCID 19737997, compound

HRID 2255506Notes

Reaction equation

HRID 2255506 reaction equation
[OH:1][CH:2]1[C:7]2[CH:8]=[CH:9][S:10][C:6]=2[S:5](=[O:12])(=[O:11])[NH:4][CH2:3]1.[H-].[Na+].[CH2:15](Br)[CH:16]=[CH2:17]>CN(C=O)C>[CH2:17]([N:4]1[CH2:3][CH:2]([OH:1])[C:7]2[CH:8]=[CH:9][S:10][C:6]=2[S:5]1(=[O:12])=[O:11])[CH:16]=[CH2:15]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 229019424-Hydroxy-3,4-dihydro-1lambda~6~-thieno[3,2-e][1,2]thiazine-1,1(2H)-dione

Product 1

HCID 19737997HCID 19737997, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
-10 °C

Procedure

The product from Step C of Example 2 (4.0 g, 19.5 mmol) was dissolved in anhydrous DMF (70 mL) cooled to -10° C. and sodium hydride (21.5 mmol) was added. After stirring for five minutes allyl bromide (2.53 mL, 29.25 mmol) was added and this mixture stirred for 2 h at 0° C. The reaction mixture was poured onto ice water (100 mL) and this solution was extracted with ethyl acetate. The combined extracts were washed with brine, dried (MgSO4) and evaporated to give a crude product which was purified by column chromatography (silica, methylene chloride:methanol, 20:1) to provide the desired product (4.2 g, 88%) as a syrup.

Workup

  1. additionwas added
  2. additionThe reaction mixture was poured onto ice water (100 mL)
  3. extractionthis solution was extracted with ethyl acetate
  4. washThe combined extracts were washed with brine
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customto give a crude product which
  8. customwas purified by column chromatography (silica, methylene chloride:methanol, 20:1)

Sources & evidence

ORD record
ord-787f612a7ee14d269243e2299d5df1d9
Source dataset
uspto-grants-1993_08
Patent number
US05240923

Reaction notes

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