Reaction #985259

Reaction equation

4-methoxy-4′-nitrothiobenzaniline

4-Methoxy-4′-nitrobenzanilide

Lawesson's reagent

→

product 4

Yield 129.3%

4-Methoxy-4′-nitrothiobenzanilide

Yield 129.3%

Solvents

chlorobenzene

Conditions

Workup

1. 1
   Temperaturewas heated
2. 2
   Temperatureto reflux for 4 hrs
3. 3
   OtherThe solvent was evaporated
4. 4
   Otherthe residue was purified
5. 5
   Otherwith flush column (hexane:ethyl acetate=4:1)

Procedure

A mixture of 4-methoxy-4′-nitrothiobenzaniline 3 (1.0 g, 3.7 mmol) and Lawesson's reagent (0.89 g, 2.2 mmol, 0.6 equiv.) in chlorobenzene (15 mL) was heated to reflux for 4 hrs. The solvent was evaporated and the residue was purified with flush column (hexane:ethyl acetate=4:1) to give 820 mg (77.4%) of the product 4 as orange color solid. 1HNMR(300 MHz, DMSO-d6) δ: 8.29(d, 2H, H-3′,5′), 8.00(d, J=8.5 Hz, 2H, H-2′,6′), 7.76(d, 2H), 7.03(d, J=8.4 Hz, 2H), 3.808.37(d, J=5.5 Hz, 2H, H-3′,5′), 8.17(d, J=6.3 Hz, 2H, H-2′, 6′), 7.48(d, J=6.6 Hz, 2H), 6.97(d, J=6.5 Hz, 2H), 3.75(s, 3H, MeO). (s, 3H, MeO).

Source