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

HRID 723881Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 723881
[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]

Komponenten

4

Edukt 2

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

Produkt 1

HCID 86610078N'-(2-fluoro-4-nitro-thiobenzoyl)hydrazinecarboxylic acid tert-butyl esterAusbeute 110,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-f4d66e9552604d238968faf06989a916
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07141588B2

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