Dimethyl Sulfide → 3-(2-Methyl-6-methylthiophenyl)-4,5-dihydroisoxazole

HRID 49667

반응식

HRID 49667 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]C>[Cu]Cl>[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 1068Dimethyl SulfideHCID 10996Butyl nitriteHCID 97940062-(4,5-Dihydroisoxazol-3-yl)-3-methylaniline

생성물 1

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

시약·촉매·용매 1

HCID 62652Cuprous chloride촉매

반응 조건

온도
60 °C

실험 절차

40 g (0.22 mol) of 2-(4,5-dihydroisoxazol-3-yl)-3-methylaniline and 0.44 g of copper(I) chloride are initially charged in 300 ml of dimethyl sulfide, 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 mixture is then washed with dilute hydrochloric acid and water and then concentrated under reduced pressure. This gives 38.7 g (85%) of a dark oil which solidifies after a while (content according to HPLC 94%). The product can be purified further by trituration in methyl tert-butyl ether.

후처리

  1. washFor work-up, the mixture is then washed with dilute hydrochloric acid and water
  2. concentrationconcentrated under reduced pressure
  3. customThe product can be purified further by trituration in methyl tert-butyl ether

출처 및 근거

ORD 기록
ord-eebd678ebf0344898ce01b01fd0724f3
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06706886B2

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