Tert-Butyl nitrite → 250593-00-1

HRID 1061113Notes

Reaction equation

HRID 1061113 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 50-58° C. The mixture is then stirred at 75-80° 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, excess dimethyl disulfide is removed under atmospheric pressure. 1870 g of dimethyl disulfide (purity >97% according to GC) are recovered. The residue is then 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, excess dimethyl disulfide is removed under atmospheric pressure
  7. custom1870 g of dimethyl disulfide (purity >97% according to GC) are recovered
  8. distillationThe residue is then subjected to fractional distillation under reduced pressure (0.1 mbar)

Sources & evidence

ORD record
ord-d51500dc2f5e4f4dbf5373c1437b2f26
Source dataset
uspto-grants-2003_02
Patent number
US06525204B1

Reaction notes

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