Allyl bromide → 4-(2-fluoro-4-nitrophenyl)tetrahydro-2-(2-propenyl)-2H-1,2-thiazine 1,1-dioxide

HRID 1699657Notes

Reaction equation

HRID 1699657 reaction equation
C(=O)([O-])[O-].[K+].[K+].[F:7][C:8]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[CH:11]=[CH:10][C:9]=1[CH:17]1[CH2:22][CH2:21][S:20](=[O:24])(=[O:23])[NH:19][CH2:18]1.[CH2:25](Br)[CH:26]=[CH2:27]>C(#N)C>[F:7][C:8]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[CH:11]=[CH:10][C:9]=1[CH:17]1[CH2:22][CH2:21][S:20](=[O:24])(=[O:23])[N:19]([CH2:27][CH:26]=[CH2:25])[CH2:18]1

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 183691484-(2-Fluoro-4-nitrophenyl)tetrahydro-2H-1,2-thiazine 1,1-dioxide

Product 1

HCID 183691474-(2-fluoro-4-nitrophenyl)tetrahydro-2-(2-propenyl)-2H-1,2-thiazine 1,1-dioxide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Anhydrous potassium carbonate (3.6 g, 26.1 mmol) is added to a solution of 4-(2-fluoro-4-nitrophenyl)tetrahydro-2 H-1,2-thiazine 1,1-dioxide (1.795 g, 6.54 mmol) and allyl bromide (2.0 ml, 23.1 mmol) in dry acetonitrile (25 ml). The mixture is heated to reflux for 5 min then cooled. After filtration and evaporation the residue is chromatographed over silica gel (150 g) eluting with 0-1% methanol-chloroform. The title compound is obtained as flakes (1.70 g, 83%) mp 121°.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux for 5 min
  3. temperaturethen cooled
  4. filtrationAfter filtration and evaporation the residue
  5. customis chromatographed over silica gel (150 g)
  6. washeluting with 0-1% methanol-chloroform

Sources & evidence

ORD record
ord-efc8630e710b4ff19966a532137534f6
Source dataset
uspto-grants-2002_02
Patent number
US06348459B1

Reaction notes

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