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

HRID 2229128Notes

Reaction equation

HRID 2229128 reaction equation
[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]

Participants

7

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-087fd7205f78448781eff21a8bfc4e70
Source dataset
uspto-grants-2002_07
Patent number
US06420362B1

Reaction notes

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