Lawesson's reagent → Tert-butyl Dithiobenzoate

HRID 1297484Notes

Reaction equation

HRID 1297484 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

HCID 9920756Tert-butyl Dithiobenzoate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-8949f31816ee4daca5bc17dfab4aef56
Source dataset
uspto-grants-2007_07
Patent number
US07250479B2

Reaction notes

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