Dimethyl 2,2'-dithiobisbenzoate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 25 g (81.6 mmol) of dithiodibenzoic acid is refluxed in 60 ml of SOCl2 and 1.5 ml of dimethylformamide (DMF) for 3 hrs. Then the excess of SOCl2 is distilled off, and the residue is dissolved in CHCl3 and added dropwise to a solution of methanol (50 ml) and triethylamine (0.204 mol) in CHCl3 (300 l). After standing over night the reaction mixture is shaked with water and saturated K2CO3 solution. After drying the organic layer the solvent is evaporated and methanol is added to the residue (oil). 13.6 g (50%) of solid product is obtained. Then the excess of SOCl2 is distilled off the residue is dissolved in CHCl3 After standing over night After drying the organic layer the solvent is evaporated methanol is added to the residue (oil)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 6 mL Sulphuric acid is added to ‘2,2’-dithiodibenzoic acid (20 g, 65.3 mmol) in 150 mL methanol. The reaction mixture is refluxed 3 days. The reaction mixture is cooled to room temperature and saturated aqueous NaHCO3 is added. Methanol is removed in vacuo. The resulting heterogeneous mixture is extracted with ethyl acetate. The organic phase is washed with brine, dried with MgSO4 and concentrated in vacuo to give 17.8 g (82%) of the title compound as a solid, which is used without further purification. The reaction mixture is refluxed 3 days Methanol is removed in vacuo The resulting heterogeneous mixture is extracted with ethyl acetate The organic phase is washed with brine dried with MgSO4 concentrated in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 6 mL Sulphuric acid is added to ‘2,2’-dithiodibenzoic acid (20 g, 65.3 mmol) in 150 mL methanol. The reaction mixture is refluxed 3 days. The reaction mixture is cooled to room temperature and saturated aqueous NaHCO3 is added. Methanol is removed in vacuo. The resulting heterogeneous mixture is extracted with ethyl acetate. The organic phase is washed with brine, dried with MgSO4 and concentrated in vacuo to give 17.8 g (82%) of the title compound as a solid, which is used without further purification. The reaction mixture is refluxed 3 days Methanol is removed in vacuo The resulting heterogeneous mixture is extracted with ethyl acetate The organic phase is washed with brine dried with MgSO4 concentrated in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 25 g (81.6 mmol) of dithiodibenzoic acid is refluxed in 60 ml of SOCl2 and 1.5 ml of dimethylformamide (DMF) for 3 hrs. Then the excess of SOCl2 is distilled off, and the residue is dissolved in CHCl3 and added dropwise to a solution of methanol (50 ml) and triethylamine (0.204 mol) in CHCl3 (300 l). After standing over night the reaction mixture is shaked with water and saturated K2CO3 solution. After drying the organic layer the solvent is evaporated and methanol is added to the residue (oil). 13.6 g (50%) of solid product is obtained. Then the excess of SOCl2 is distilled off the residue is dissolved in CHCl3 After standing over night After drying the organic layer the solvent is evaporated methanol is added to the residue (oil)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 6 mL Sulphuric acid is added to ‘2,2’-dithiodibenzoic acid (20 g, 65.3 mmol) in 150 mL methanol. The reaction mixture is refluxed 3 days. The reaction mixture is cooled to room temperature and saturated aqueous NaHCO3 is added. Methanol is removed in vacuo. The resulting heterogeneous mixture is extracted with ethyl acetate. The organic phase is washed with brine, dried with MgSO4 and concentrated in vacuo to give 17.8 g (82%) of the title compound as a solid, which is used without further purification. The reaction mixture is refluxed 3 days Methanol is removed in vacuo The resulting heterogeneous mixture is extracted with ethyl acetate The organic phase is washed with brine dried with MgSO4 concentrated in vacuo