Hexane → 2-[2-(Benzenesulfonyl)-ethylsulfanyl]-3-nitropyridine

HRID 888259

Reaktionsgleichung

Reaktionsgleichung von HRID 888259
CC([O-])(C)C.[K+].[C:7]1([S:13]([CH2:16][CH2:17][SH:18])(=[O:15])=[O:14])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.Cl[C:20]1[C:25]([N+:26]([O-:28])=[O:27])=[CH:24][CH:23]=[CH:22][N:21]=1.CCCCCC>CN(C=O)C.[Cl-].[Na+].O>[C:7]1([S:13]([CH2:16][CH2:17][S:18][C:20]2[C:25]([N+:26]([O-:28])=[O:27])=[CH:24][CH:23]=[CH:22][N:21]=2)(=[O:15])=[O:14])[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Komponenten

7

Edukt 4

HCID 8058HexaneHCID 796132-Chloro-3-nitropyridineHCID 4470932-(Phenylsulfonyl)ethanethiolHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 671337572-[2-(Benzenesulfonyl)-ethylsulfanyl]-3-nitropyridineAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

1.8 g (16.0 mmol) potassium tert-butylate were added to a solution of 3.0 g (14.8 mmol) 2-(phenylsulfonyl)ethanethiol in DMF (35 ml) and the mixture was stirred for 30 min at room temperature. Then 2.5 g (15.8 mmol) 2-chloro-3-nitropyridine were added and the mixture was stirred for a further 1 h at RT. Then it was diluted with a brine/EE mixture (1:1 vv) and stirred for a further 30 min at RT. Then the organic phase was separated off, washed with water and brine, dried over Na2SO4, filtered and concentrated to small volume under vacuum. Column chromatography (hexane/EE 6:1) of the residue yielded 2.2 g (6.8 mmol, 46%) 2-[2-(benzenesulfonyl)-ethylsulfanyl]-3-nitropyridine.

Aufarbeitung

  1. stirringthe mixture was stirred for a further 1 h at RT
  2. stirringstirred for a further 30 min at RT
  3. customThen the organic phase was separated off
  4. washwashed with water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated to small volume under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-6cd212b40b0f4f10b0d04144f712bace
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08247573B2

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