Tert-Butyl nitrite → 3-(2-Methyl-6-methylthiophenyl)-4,5-dihydroisoxazole

HRID 49664

Reaction equation

HRID 49664 reaction equation
C(ON=O)(C)(C)C.[O:8]1[CH2:12][CH2:11][C:10]([C:13]2[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][C:14]=2N)=[N:9]1.[CH3:21][S:22]SC>[Cu]>[CH3:20][C:19]1[CH:18]=[CH:17][CH:16]=[C:14]([S:22][CH3:21])[C:13]=1[C:10]1[CH2:11][CH2:12][O:8][N:9]=1

Participants

5

Reactant 3

HCID 10906Tert-Butyl nitriteHCID 12232Dimethyl Disulfide2×HCID 97940062-(4,5-Dihydroisoxazol-3-yl)-3-methylaniline

Product 1

HCID 108783423-(2-Methyl-6-methylthiophenyl)-4,5-dihydroisoxazole

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Conditions

Temperature
60 °C

Procedure

19.5 g (170 mmol) of tert-butylnitrite and 20 g of copper powder are initially charged in 30 ml of dimethyl disulfide, and a solution of 20 g (114 mmol) of 2-(4,5-dihydroisoxazol-3-yl)-3-methylaniline in 100 ml of dimethyl disulfide is added dropwise at from 50 to 55° C. The mixture is subsequently stirred at 60° C. for 1.5 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 and dried over sodium sulfate, the drying agent is filtered off and the filtrate is concentrated. Excess dimethyl disulfide is removed under oil pump vacuum.

Workup

  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. filtrationthe drying agent is filtered off
  7. concentrationthe filtrate is concentrated
  8. customExcess dimethyl disulfide is removed under oil pump vacuum

Sources & evidence

ORD record
ord-225b4e59ac194d10aa7e481d914525c0
Source dataset
uspto-grants-2004_03
Patent number
US06706886B2

Linked notes

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