Tert-Butyl nitrite → HCID 18446121, compound

HRID 460504Notes

Reaction equation

HRID 460504 reaction equation
N(OC(C)(C)C)=O.[Br:8][C:9]1[CH:15]=[CH:14][C:12](N)=[C:11]([S:16]([CH3:19])(=[O:18])=[O:17])[C:10]=1[CH3:20].[CH3:21][S:22]SC>[Cu]>[Br:8][C:9]1[CH:15]=[CH:14][C:12]([S:22][CH3:21])=[C:11]([S:16]([CH3:19])(=[O:18])=[O:17])[C:10]=1[CH3:20]

Participants

5

Reactant 3

HCID 10906Tert-Butyl nitriteHCID 12232Dimethyl Disulfide2×HCID 184461204-Bromo-3-methyl-2-methylsulfonylaniline

Product 1

HCID 18446121HCID 18446121, compound

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Procedure

75 g of copper powder and 100 ml of dimethyl disulfide were added to 92 g (0.8 mol) of tert-butyl nitrite. At 50–52° C., a solution of 142 g (0.54 mol) of 4-bromo-3-methyl-2-methylsulfonyl aniline in 600 ml of dimethyl disulfide was added dropwise, and the mixture was stirred at 50–55° C. for 7 hours. After cooling, the mixture was filtered off with suction through kieselguhr, and dichloromethane was added to the filtrate. The organic phase was washed with dilute hydrochloric acid and then with water. After drying over sodium sulfate, the organic phase was concentrated under high vacuum. This gave 170 g of the title compound as a black oil which was used for the next reaction step without further purification.

Workup

  1. temperatureAfter cooling
  2. filtrationthe mixture was filtered off with suction through kieselguhr, and dichloromethane
  3. additionwas added to the filtrate
  4. washThe organic phase was washed with dilute hydrochloric acid
  5. dry with materialAfter drying over sodium sulfate
  6. concentrationthe organic phase was concentrated under high vacuum
  7. customThis gave 170 g of the title compound as a black oil which was used for the next reaction step without further purification

Sources & evidence

ORD record
ord-a881e726e1a6408c8e022af07c53ad6d
Source dataset
uspto-grants-2007_03
Patent number
US07196229B2

Reaction notes

Loading…