Phosphorus sulfide (P2S5) → 8-Fluoro-2,2-dimethyl-6-nitro-2H-benzo[b][1,4]oxazin-3(4H)-thione

HRID 1754410Notes

Reaction equation

HRID 1754410 reaction equation
[F:1][C:2]1[C:7]2[O:8][C:9]([CH3:14])([CH3:13])[C:10](=O)[NH:11][C:6]=2[CH:5]=[C:4]([N+:15]([O-:17])=[O:16])[CH:3]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:19]>C1COCC1>[F:1][C:2]1[C:7]2[O:8][C:9]([CH3:14])([CH3:13])[C:10](=[S:19])[NH:11][C:6]=2[CH:5]=[C:4]([N+:15]([O-:17])=[O:16])[CH:3]=1

Participants

4

Reactant 2

HCID 14817Phosphorus sulfide (P2S5)HCID 898638688-Fluoro-2,2-dimethyl-6-nitro-2H-benzo[b][1,4]oxazin-3(4H)-one

Product 1

HCID 898638698-Fluoro-2,2-dimethyl-6-nitro-2H-benzo[b][1,4]oxazin-3(4H)-thioneYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 8-Fluoro-2,2-dimethyl-6-nitro-2H-benzo[b][1,4]oxazin-3(4H)-one (0.75 g, 3.1 mmol) in 25 ml anhydrous THF, P2S5 (2.8 g, 6.25 mmol) was added and the reaction mixture was heated to reflux for 12 hours. Analysis of LC-MS indicated the completion of the reaction. Volatiles were removed in vacuo and the crude reaction mixture was partitioned in EtOAc (100 ml) and saturated aqueous NH4Cl (100 ml). Layers were separated and the organic layer was washed (×2) with saturated aqueous NH4Cl (50 ml). EtOAc layer was dried over Na2SO4 and concentrated to give the product in 69% yield (0.55 g). LCMS (m/z) 257 (MH+).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 12 hours
  3. customthe completion of the reaction
  4. customVolatiles were removed in vacuo
  5. customthe crude reaction mixture
  6. customwas partitioned in EtOAc (100 ml)
  7. customLayers were separated
  8. washthe organic layer was washed (×2) with saturated aqueous NH4Cl (50 ml)
  9. dry with materialEtOAc layer was dried over Na2SO4
  10. concentrationconcentrated
  11. customto give the product in 69% yield (0.55 g)

Sources & evidence

ORD record
ord-f4e8365b4df64e4bb69cfff6df1cff89
Source dataset
uspto-grants-2015_10
Patent number
US09169249B2

Reaction notes

Loading…