Lawesson's reagent → Tert-butyl Dithiobenzoate

HRID 1297484Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1297484
[C:1]([S:9][C:10]([CH3:13])([CH3:12])[CH3:11])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:23])=CC=1>C1(C)C=CC=CC=1>[C:1]([S:9][C:10]([CH3:13])([CH3:12])[CH3:11])(=[S:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 87949Lawesson's reagentHCID 12492106S-tert-Butyl benzenecarbothioate

Produkt 1

HCID 9920756Tert-butyl Dithiobenzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of S-t-butyl thiobenzoate (1.94 g, 0.01 mol) and Lawesson's reagent (2.43 g, 0.006 mol) in anhydrous toluene (10 mL) was refluxed for 25 hours. After cooling to room temperature, the reaction mixture was concentrated and the residue subjected to column chromatography (Kieselgel-60, 70-230 mesh, petroleum spirit/diethyl ether 19:1) The title compound was obtained as an oil, 1.37 g (65.5%). 1H-nmr (CDCl3) d (ppm): 1.69 (s, 9H, 3×CH3), 7.36 (m, 2H, meta-ArH), 7.50 (m, 1H, para-ArH) and 7.88 (d, 2H, ortho-ArH). 13C-nmr (CDCl3) d (ppm): 28.2, 52.2, 126.6, 128.1, 131.7 and 147.0. The signal due to C═S (d>220.0 ppm) was beyond the frequency range of the spectrum.

Aufarbeitung

  1. temperaturewas refluxed for 25 hours
  2. concentrationthe reaction mixture was concentrated
  3. customwas obtained as an oil, 1.37 g (65.5%)

Quellen und Nachweise

ORD-Eintrag
ord-8949f31816ee4daca5bc17dfab4aef56
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07250479B2

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