Tert-Butyl nitrite → 2-Methyl-6-nitrothioanisole

HRID 49681

Reaktionsgleichung

Reaktionsgleichung von HRID 49681
N(OC(C)(C)C)=O.[CH3:8][C:9]1[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-:18])=[O:17])[C:10]=1N.[CH3:19][S:20]SC>[Cu]>[CH3:8][C:9]1[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-:18])=[O:17])[C:10]=1[S:20][CH3:19]

Komponenten

5

Edukt 3

HCID 10906Tert-Butyl nitriteHCID 112982-Methyl-6-nitroanilineHCID 12232Dimethyl Disulfide2×

Produkt 1

HCID 187572722-Methyl-6-nitrothioanisole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 23978CopperKatalysator

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

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%.

Aufarbeitung

  1. filtrationFor work-up, the solid is filtered off with suction
  2. additionthe filtrate is diluted with methylene chloride
  3. extractionextracted with dilute hydrochloric acid
  4. washThe organic phase is washed with saturated aqueous NaHCO3 solution
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered off
  7. concentrationconcentrated
  8. customExcess dimethyl disulfide is removed under oil pump vacuum

Quellen und Nachweise

ORD-Eintrag
ord-386dca9a8cd840e7b83c2ebe367202a1
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06706886B2

Verknüpfte Notizen

Wird geladen…