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

HRID 49664

반응식

HRID 49664 반응식
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

참가 물질

5

반응물 3

HCID 10906Tert-Butyl nitriteHCID 12232Dimethyl Disulfide2회HCID 97940062-(4,5-Dihydroisoxazol-3-yl)-3-methylaniline

생성물 1

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

시약·촉매·용매 1

HCID 23978Copper촉매

반응 조건

온도
60 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-225b4e59ac194d10aa7e481d914525c0
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06706886B2

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