Lawesson's reagent → N'-(2-fluoro-4-nitro-thiobenzoyl)hydrazinecarboxylic acid tert-butyl ester

HRID 896157Notes

Reaction equation

HRID 896157 reaction equation
[C:1]([O:5][C:6]([NH:8][NH:9][C:10](=O)[C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][C:12]=1[F:20])=[O:7])([CH3:4])([CH3:3])[CH3:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:31])=CC=1>O1CCOCC1>[C:1]([O:5][C:6]([NH:8][NH:9][C:10](=[S:31])[C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][C:12]=1[F:20])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 68487050N'-(2-fluoro-4-nitrobenzoyl)hydrazinecarboxylic acid tert-butyl ester

Product 1

HCID 86610078N'-(2-fluoro-4-nitro-thiobenzoyl)hydrazinecarboxylic acid tert-butyl esterYield 110.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

N′-(2-Fluoro-4-nitro-benzoyl)hydrazinecarboxylic acid tert-butyl ester (Step 1, 2.32 g, 7.75 mmol) and Lawesson's reagent (2.35 g, 5.81 mmol) in dioxane (50 ml) are heated at 85° C. overnight. The mixture is evaporated under vacuum and the residue purified by flash column chromatography (70% dichloromethane/hexane) to give the title compound as a bright orange solid (2.02 g, 82%), [M+H]+=316.

Workup

  1. customThe mixture is evaporated under vacuum
  2. customthe residue purified by flash column chromatography (70% dichloromethane/hexane)

Sources & evidence

ORD record
ord-8e7d59ecca2f48d0961d1b270a9ffd95
Source dataset
uspto-grants-2005_07
Patent number
US06919329B2

Reaction notes

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