p-Toluenesulfonic acid → (5,6-dihydro-[1,4,2]dioxazin-3-yl)-(2-{[1-(3-trifluoromethylphenyl)-ethylidene]-hydrazonomethyl}-phenyl)-methanone O-methyl oxime

HRID 2229128노트

반응식

HRID 2229128 반응식
[O:1]1[CH2:6][CH2:5][O:4][C:3]([C:7](=[N:16][O:17][CH3:18])[C:8]2[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=2[CH:10]=O)=[N:2]1.[CH3:19][C:20]([C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=1)=O.O.[NH2:33][NH2:34].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.O>[CH3:18][O:17][N:16]=[C:7]([C:3]1[O:4][CH2:5][CH2:6][O:1][N:2]=1)[C:8]1[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=1[CH:10]=[N:33][N:34]=[C:20]([C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=1)[CH3:19]

참가 물질

7

반응물 4

HCID 6101p-Toluenesulfonic acidHCID 24654Hydrazine hydrate (1:1)HCID 676823'-(Trifluoromethyl)acetophenoneHCID 542963122-[(5,6-Dihydro-[1,4,2]dioxazin-3-yl)-methoxyimino-methyl]-benzaldehyde

생성물 1

HCID 73864786(5,6-dihydro-[1,4,2]dioxazin-3-yl)-(2-{[1-(3-trifluoromethylphenyl)-ethylidene]-hydrazonomethyl}-phenyl)-methanone O-methyl oxime수율 29%

시약·촉매·용매 2

HCID 962Water용매HCID 1140Toluene용매

실험 절차

0.9 g (0.0036 mol) of 2-[(5,6-dihydro-[1,4,2]dioxazin-3-yl)-methoxyimino-methyl]-benzaldehyde, 0.69 g (0.0036 mol) of 3-trifluoromethylacetophenone, 0.18 g (0.0036 mol) of hydrazine hydrate and 25 mg of 4-toluenesulphonic acid are heated under reflux in 120 ml of toluene for 18 hours using a water separator. After cooling, the mixture is dried over magnesium sulphate and concentrated under reduced pressure. The residue is chromatographed over silica gel with cyclohexane/ethyl acetate (5:1). 0.45 g (29% of theory) of (5,6-dihydro-[1,4,2]dioxazin-3-yl)-(2-{[1-(3-trifluoromethylphenyl)-ethylidene]-hydrazonomethyl}-phenyl)-methanone O-methyl oxime is obtained.

후처리

  1. temperatureAfter cooling
  2. dry with materialthe mixture is dried over magnesium sulphate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue is chromatographed over silica gel with cyclohexane/ethyl acetate (5:1)

출처 및 근거

ORD 기록
ord-087fd7205f78448781eff21a8bfc4e70
출처 데이터셋
uspto-grants-2002_07
특허 번호
US06420362B1

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