Lawesson's reagent → 2,2-dimethyl-6-nitro-2H-benzo[b][1,4]oxazine-3(4H)-thione

HRID 633453Notes

Reaction equation

HRID 633453 reaction equation
[CH3:1][C:2]1([CH3:16])[O:7][C:6]2[CH:8]=[CH:9][C:10]([N+:12]([O-:14])=[O:13])=[CH:11][C:5]=2[NH:4][C:3]1=O.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:26])=CC=1>C1(C)C=CC=CC=1>[CH3:1][C:2]1([CH3:16])[O:7][C:6]2[CH:8]=[CH:9][C:10]([N+:12]([O-:14])=[O:13])=[CH:11][C:5]=2[NH:4][C:3]1=[S:26]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 106566312,2-Dimethyl-6-nitro-2H-benzo[B][1,4]oxazin-3(4H)-one

Product 1

HCID 594105272,2-dimethyl-6-nitro-2H-benzo[b][1,4]oxazine-3(4H)-thioneYield 82.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2,2-Dimethyl-6-nitro-2H-benzo[b][1,4]oxazin-3(4H)-one (3.4 g) and Lawesson's reagent (6.19 g, 1.0 eq.) were suspended in toluene (100 ml). The reaction mixture was refluxed for one hour. The mixture was then evaporated. The residue was purified by Combiflash chromatography (EtOAc in hexanes=0-100%) to give 2,2-dimethyl-6-nitro-2H-benzo[b][1,4]oxazine-3(4H)-thione (3 g, 82% yield).

Workup

  1. temperatureThe reaction mixture was refluxed for one hour
  2. customThe mixture was then evaporated
  3. customThe residue was purified by Combiflash chromatography (EtOAc in hexanes=0-100%)

Sources & evidence

ORD record
ord-f7022769ef164b6e8225719bef8ba1ee
Source dataset
uspto-grants-2016_04
Patent number
US09321763B2

Reaction notes

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