Water → 4-Methyl-6-(methylsulfonyl)pyridin-3-amine

HRID 1811567

Reaktionsgleichung

Reaktionsgleichung von HRID 1811567
Cl[C:2]1[N:7]=[CH:6][C:5]([NH2:8])=[C:4]([CH3:9])[CH:3]=1.[CH3:10][S:11]([O-:13])=[O:12].[Na+].CNCCNC.O>[Cu].CS(C)=O>[CH3:10][S:11]([C:2]1[N:7]=[CH:6][C:5]([NH2:8])=[C:4]([CH3:9])[CH:3]=1)(=[O:13])=[O:12]

Komponenten

7

Edukt 4

HCID 962WaterHCID 8070N,N'-DimethylethylenediamineHCID 2733271Sodium methanesulfinateHCID 27344253-Amino-6-chloro-4-picoline

Produkt 1

HCID 586715824-Methyl-6-(methylsulfonyl)pyridin-3-amineAusbeute 27 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23978CopperKatalysatorHCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

A mixture of 6-chloro-4-methyl-pyridin-3-ylamine (1.53 g, 11 mmol), sodium methanesulfinate (1.60 g, 16 mmol), copper catalyst (0.50 g, 0.99 mmol), and N1,N2-dimethylethane-1,2-diamine (0.214 mL, 2.0 mmol) in 20 mL DMSO was heated under microwave irradiation at 150° C. After 2 h, mixture was poured into ca. 200 mL water and extracted five times with ca. 200 mL AcOEt. Organic phases were dried over MgSO4, filtered, and concentrated. Residue was purified by column chromatography (AcOEt/hexane 5:1→AcOEt) to give 6-methanesulfonyl-4-methyl-pyridin-3-ylamine as a white solid (0.534 g, 27%). 1HNMR (DMSO-d6, 400 MHz) 32.4 (s, 3H), 3.08 (s, 3H), 6.08 (s, 2H), 7.59 (s, 1H), 7.97 (s, 1H). Exact mass calculated for C7H10N2O2S 186.05 found 187.0 (MH+).

Aufarbeitung

  1. extractionextracted five times with ca. 200 mL AcOEt
  2. dry with materialOrganic phases were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customResidue was purified by column chromatography (AcOEt/hexane 5:1→AcOEt)

Quellen und Nachweise

ORD-Eintrag
ord-b197c6bfbf21446cb32f5e377ae6ff9e
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08362248B2

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