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

HRID 2229128ノート

反応式

HRID 2229128 の反応式
[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]

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1140Toluene溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-087fd7205f78448781eff21a8bfc4e70
出典データセット
uspto-grants-2002_07
特許番号
US06420362B1

反応ノート

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