Dimethylformamide → 4-(4-Methoxybenzylthio)-2-chloropyridine

HRID 911051Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 911051
[Cl:1][C:2]1[CH:7]=[C:6]([N+]([O-])=O)[CH:5]=[CH:4][N:3]=1.[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][SH:20])=[CH:15][CH:14]=1.CN(C=O)C.C(=O)([O-])[O-].[Cs+].[Cs+]>ClCCl>[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][S:20][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([Cl:1])[CH:7]=2)=[CH:15][CH:14]=1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 804074-Methoxy-alpha-toluenethiolHCID 7351522-Chloro-4-nitropyridine

Produkt 1

HCID 866347684-(4-Methoxybenzylthio)-2-chloropyridineAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A flask was charged with 2-chloro-4-nitropyridine (12.75 g, 80.4 mmol), (4-methoxyphenyl)methanethiol (12.40 g, 80.4 mmol) and DMF (100 mL). Cesium carbonate (31.43 g, 96.48 mmol) was added in portions, and the mixture was stirred for 2 hours at ambient temperature. The solution was diluted with dichloromethane (250 mL) and washed with diluted sodium bicarbonate solution, dried over magnesium sulfate, filtered and evaporated. The resulting yellowish residue was triturated with hexanes and the solid was filtered to obtain the desired product (18.1 g, 85%) as a pale yellow powder.

Aufarbeitung

  1. washwashed with diluted sodium bicarbonate solution
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe resulting yellowish residue was triturated with hexanes
  6. filtrationthe solid was filtered

Quellen und Nachweise

ORD-Eintrag
ord-66fd79e2f5ae454cabdc87966c4f083e
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08022222B2

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