1,3-Dichloro-5,5-dimethylhydantoin → 3-Nitropyridine-2-sulfonyl chloride

HRID 424275

Reaktionsgleichung

C(S[C:9]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][CH:12]=[CH:11][N:10]=1)C1C=CC=CC=1.[Cl:18]N1C(C)(C)C(=O)N(Cl)C1=O.[S:29](S([O-])=O)([O-:32])(=O)=[O:30].[Na+].[Na+].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>ClCCl.O.C(O)(=O)C>[N+:15]([C:14]1[C:9]([S:29]([Cl:18])(=[O:32])=[O:30])=[N:10][CH:11]=[CH:12][CH:13]=1)([O-:17])=[O:16]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

2-Benzylsulfanyl-3-nitro-pyridine (6 g, 24.39 mmol) was dissolved in dichloromethane (84 mL). Acetic acid (12 mL) and water (24 mL) were added. The mixture was chilled to 0° C. With vigorous stirring, 1,3-dichloro-5,5-dimethyl-imidazolidine-2,4-dione (14.4 g, 73.17 mmol) was added portionwise as a suspension in dichloromethane (48 mL). The mixture was allowed to slowly warm to 25° C. and continued to stir for 16 h. The mixture was poured into 5% aqueous sodium metabisulfite solution (100 mL) and shaken well. Dichloromethane (200 mL) and 20% aqueous dibasic potassium phosphate solution (100 mL) were added and the mixture was shaken well. The layers were separated. The crude desired product, 3-nitro-pyridine-2-sulfonyl chloride, dissolved in the organic layer was used directly in the next step without further isolation or characterization.

Aufarbeitung

temperatureto slowly warm to 25° C.
stirringshaken well
stirringthe mixture was shaken well
customThe layers were separated
dissolutionThe crude desired product, 3-nitro-pyridine-2-sulfonyl chloride, dissolved in the organic layer

Quellen und Nachweise

ORD-Eintrag: ord-8f38c9d00d024a55af7dc573dd6acad9
Quelldatensatz: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08101800B2

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