Reaktion #77959

Reaktionsgleichung

tert-butyl nitrite

dimethyl disulfide

2-methyl-6-nitroaniline

dimethyl disulfide

→

2-methyl-6-nitrothioanisole

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationFor work-up, the solid is filtered off with suction
2. 2
   workup.ADDITIONthe filtrate is diluted with methylene chloride
3. 3
   Extraktionextracted with dilute hydrochloric acid
4. 4
   WaschenThe organic phase is washed with saturated aqueous NaHCO3 solution
5. 5
   Trocknendried over sodium sulfate
6. 6
   Filtrationfiltered off
7. 7
   Einengenconcentrated
8. 8
   SonstigeExcess dimethyl disulfide is removed under oil pump vacuum

Vorschrift

226 g (1.97 mol) of tert-butyl nitrite and 100 g of copper powder are initially charged in 300 ml of dimethyl disulfide, and a solution of 200 g (1.32 mol) of 2-methyl-6-nitroaniline in 700 ml of dimethyl disulfide is added dropwise at from 50 to 55° C. The mixture is subsequently stirred at 75° C. for 8 hours. For work-up, the solid is filtered off with suction and the filtrate is diluted with methylene chloride and extracted with dilute hydrochloric acid. The organic phase is washed with saturated aqueous NaHCO3 solution, dried over sodium sulfate, filtered off and concentrated. Excess dimethyl disulfide is removed under oil pump vacuum. This gives 271 g (99%) of a dark-red oil, purity according to HPLC 87%.

Quelle