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

HRID 49665

반응식

HRID 49665 반응식
[O:1]1[CH2:5][CH2:4][C:3]([C:6]2[C:12]([CH3:13])=[CH:11][CH:10]=[CH:9][C:7]=2N)=[N:2]1.N(OCCCC)=O.[CH3:21][S:22]SC>[Cu]>[CH3:13][C:12]1[CH:11]=[CH:10][CH:9]=[C:7]([S:22][CH3:21])[C:6]=1[C:3]1[CH2:4][CH2:5][O:1][N:2]=1

참가 물질

5

반응물 3

HCID 10996Butyl nitriteHCID 12232Dimethyl DisulfideHCID 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

40 g (0.22 mol) of 2-(4,5-dihydroisoxazol-3-yl)-3-methylaniline and 1.5 g of copper powder are initially charged in 300 ml of dimethyl disulfide, and 26.1 g of n-butyl nitrite (0.23 mol) are added dropwise at 55-66° C. The mixture is then stirred at 60° C. for 1.5 hours. For work-up, the hot mixture is filtered through activated carbon and then washed with dilute hydrochloric acid and water and then concentrated under reduced pressure. This gives 44.5 g (88%) of a dark oil which solidifies after a while (content according to HPLC (95%). The product can be purified further by trituration with methyl tert-butyl ether.

후처리

  1. filtrationFor work-up, the hot mixture is filtered through activated carbon
  2. washwashed with dilute hydrochloric acid and water
  3. concentrationconcentrated under reduced pressure
  4. customThe product can be purified further by trituration with methyl tert-butyl ether

출처 및 근거

ORD 기록
ord-10d7ee252c7444df9fec62dd0a3dc293
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06706886B2

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