Lawesson's reagent → HCID 86727413, compound

HRID 519048Notes

Reaction equation

HRID 519048 reaction equation
[N+:1]([C:4]1[CH:21]=[CH:20][C:7]2[S:8][CH2:9][C:10](=O)[N:11]([CH:12]([CH3:18])[C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:6]=2[CH:5]=1)([O-:3])=[O:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:31])=CC=1>C1(C)C=CC=CC=1>[N+:1]([C:4]1[CH:21]=[CH:20][C:7]2[S:8][CH2:9][C:10](=[S:31])[N:11]([CH:12]([CH3:18])[C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:6]=2[CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 86727412HCID 86727412, compound

Product 1

HCID 86727413HCID 86727413, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of ethyl 2-(6-nitro-3-oxo-2H-benzo[b][1,4]thiazin-4(3H)-yl)propanoate (0.189 g, 0.61 mmol) and Lawesson's reagent (0.493 g, 1.22 mmol) in toluene (40 mL) was heated at reflux for 16 h. After cooling to ambient temperature, the mixture was concentrated in vacuo. The residue was purified by column chromatography on silica gel (eluting with 8% EtOAc in petroleum ether) to give ethyl 2-(6-nitro-3-thioxo-2H-benzo[b][1,4]thiazin-4(3H)-yl)propanoate (0.109 g, 55%). TLC (eluting with 25% EtOAc in petroleum ether) Rf=0.3.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 16 h
  3. concentrationthe mixture was concentrated in vacuo
  4. customThe residue was purified by column chromatography on silica gel (eluting with 8% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-4d12e645288545edb002e919f55eedac
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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