Water → 2-[(3,5-Dimethylphenyl)thio]-6-nitrobenzonitrile

HRID 835

Reaktionsgleichung

Reaktionsgleichung von HRID 835
[N+]([C:4]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-:14])=[O:13])[C:5]=1[C:6]#[N:7])([O-])=O.C([O-])([O-])=O.[K+].[K+].[CH3:21][C:22]1[CH:23]=[C:24]([SH:29])[CH:25]=[C:26]([CH3:28])[CH:27]=1.O>CN(C=O)C>[CH3:21][C:22]1[CH:23]=[C:24]([S:29][C:4]2[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-:14])=[O:13])[C:5]=2[C:6]#[N:7])[CH:25]=[C:26]([CH3:28])[CH:27]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 1175483,5-DimethylbenzenethiolHCID 520718Dinitrobenzonitrile

Produkt 1

HCID 106130552-[(3,5-Dimethylphenyl)thio]-6-nitrobenzonitrileAusbeute 73.011,203 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A mixture of 2,6-dinitrobenzonitrile (1.4 g 7.2 mmol) and K2CO3 (1.1 g, 7.9 mmol) in 10 ml of DMF was chilled to 0° C. A solution of 3,5-dimethylthiophenol (1.1 g 0.0079 mmol) in 10 ml of DMF, was added dropwise over 30 min with stirring under nitrogen. After stirring an additional 30 min, the reaction mixture was poured into 150 ml of water and stirred for 1 hr. The solid was collected by vacuum filtration. Chromatography on silica gel (flash; Hex/EtOAc 1:1) provided 1.64 g (80%) of 2-[(3,5-dimethylphenyl)thio]-6-nitrobenzonitrile: mp 155°-156° C.

Aufarbeitung

  1. stirringAfter stirring an additional 30 min
  2. stirringstirred for 1 hr
  3. filtrationThe solid was collected by vacuum filtration

Quellen und Nachweise

ORD-Eintrag
ord-942c876021324f25bb9887685a674993
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05723452

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