Tert-Butyl nitrite → 250593-00-1

HRID 49683Notes

Reaction equation

HRID 49683 reaction equation
N(OC(C)(C)C)=O.[Br:8][C:9]1[CH:15]=[CH:14][C:12](N)=[C:11]([CH3:16])[C:10]=1[CH3:17].[CH3:18][S:19]SC>[Cu]>[CH3:17][C:10]1[C:11]([CH3:16])=[C:12]([S:19][CH3:18])[CH:14]=[CH:15][C:9]=1[Br:8]

Participants

5

Reactant 3

HCID 10906Tert-Butyl nitriteHCID 12232Dimethyl DisulfideHCID 234369094-Bromo-2,3-dimethylaniline

Product 1

HCID 18757276250593-00-1

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Conditions

Temperature
77.5 °C

Procedure

603 g (5.85 mol) of tert-butyl nitrite and 375 g of copper powder (5.9 mol) are initially charged in 3000 ml of dimethyl disulfide, and 761 g (3.75 mol) of 4-bromo-2,3-dimethylaniline are added dropwise at from 50 to 58° C. The mixture is subsequently stirred at from 75 to 80° C. for 9 hours. For work-up, the mixture is cooled, the residue is filtered off and the filtrate is washed with saturated aqueous NaHCO3 solution. For purification of the product, the organic phase is separated by distillation. Initially, the excess dimethyl disulfide is separated off at atmospheric pressure. 1870 g of dimethyl disulfide (purity >97% according to GC) are recovered. The residue is subsequently subjected to fractional distillation under reduced pressure (0.1 mbar).

Workup

  1. temperatureFor work-up, the mixture is cooled
  2. filtrationthe residue is filtered off
  3. washthe filtrate is washed with saturated aqueous NaHCO3 solution
  4. customFor purification of the product
  5. customthe organic phase is separated by distillation
  6. customInitially, the excess dimethyl disulfide is separated off at atmospheric pressure
  7. custom1870 g of dimethyl disulfide (purity >97% according to GC) are recovered
  8. distillationThe residue is subsequently subjected to fractional distillation under reduced pressure (0.1 mbar)

Sources & evidence

ORD record
ord-0e1ad27a681441b7be0c91e882c72462
Source dataset
uspto-grants-2004_03
Patent number
US06706886B2

Reaction notes

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