tert-Butyl mercaptan → 1,2,4,5-Tetrakis(tert-butylthio)benzene

HRID 1048731

Reaktionsgleichung

Reaktionsgleichung von HRID 1048731
[Na].[CH3:2][C:3]([SH:6])([CH3:5])[CH3:4].Cl[C:8]1[CH:13]=[C:12](Cl)[C:11](Cl)=[CH:10][C:9]=1Cl>CN(C=O)C>[C:3]([S:6][C:8]1[CH:13]=[C:12]([S:6][C:3]([CH3:5])([CH3:4])[CH3:2])[C:11]([S:6][C:3]([CH3:5])([CH3:4])[CH3:2])=[CH:10][C:9]=1[S:6][C:3]([CH3:5])([CH3:4])[CH3:2])([CH3:5])([CH3:4])[CH3:2]

Komponenten

5

Edukt 3

HCID 6387tert-Butyl mercaptanHCID 72701,2,4,5-TetrachlorobenzeneHCID 5360545Sodium

Produkt 1

HCID 118120541,2,4,5-Tetrakis(tert-butylthio)benzeneAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Sodium (9.3 g, 0.18 mol) was added to a degassed solution of 2-methyl-2-propanethiol (20.9 mL, 0.18 mol) in dry DMF (105 mL), under stirring at 0° C. in nitrogen atmosphere. The mixture was allowed to reach room temperature (RT, 20-25° C.) and stirred overnight. 1,2,4,5-Tetrachlorobenzene (8.0 g, 0.037 mol) was then added and the resulting mixture was stirred at RT for 2 h and then gently refluxed for 18 h. After cooling at RT, the reaction mixture was poured over ice (100 g), the precipitate was removed by filtration, washed with water, and dried to give 11.0 g of the title compound as an off-white powder.

Aufarbeitung

  1. customto reach room temperature
  2. custom(RT, 20-25° C.)
  3. stirringstirred overnight
  4. stirringthe resulting mixture was stirred at RT for 2 h
  5. temperaturegently refluxed for 18 h
  6. temperatureAfter cooling at RT
  7. customthe precipitate was removed by filtration
  8. washwashed with water
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-87b806a754504fe39d1e651f26080e47
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09381257B2

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