Sulfuric acid magnesium salt (1:1) → 2-({2-[(5,6-dihydro-[1,4,2]dioxazin-3-yl)-methoxyimino-methyl]-benzylidene}-hydrazono)-1-phenylpropan-1-one O-methyl oxime

HRID 2229130Notes

Reaction equation

HRID 2229130 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:5](=[N:7][NH2:8])[CH3:6].[O:15]1[CH2:20][CH2:19][O:18][C:17]([C:21](=[N:30][O:31][CH3:32])[C:22]2[CH:29]=[CH:28][CH:27]=[CH:26][C:23]=2[CH:24]=O)=[N:16]1.S([O-])([O-])(=O)=O.[Mg+2]>C(O)C>[CH3:1][O:2][N:3]=[C:4]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:5](=[N:7][N:8]=[CH:24][C:23]1[CH:26]=[CH:27][CH:28]=[CH:29][C:22]=1[C:21]([C:17]1[O:18][CH2:19][CH2:20][O:15][N:16]=1)=[N:30][O:31][CH3:32])[CH3:6]

Participants

5

Reactant 3

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 542963122-[(5,6-Dihydro-[1,4,2]dioxazin-3-yl)-methoxyimino-methyl]-benzaldehydeHCID 572718472-hydrazono-1-phenylpropan-1-one O-methyl oxime

Product 1

HCID 725917742-({2-[(5,6-dihydro-[1,4,2]dioxazin-3-yl)-methoxyimino-methyl]-benzylidene}-hydrazono)-1-phenylpropan-1-one O-methyl oximeYield 41.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1 g (0.0052 mol) of 2-hydrazono-1-phenylpropan-1-one O-methyl oxime is heated under reflux at the boiling point in 5 ml of ethanol with 1.3 g (0.0052 mol) of 2-[(5,6-dihydro-[1,4,2]dioxazin-3-yl)-methoxyimino-methyl]-benzaldehyde and 5 g of anhydrous magnesium sulphate for 1 hour. The reaction mixture is poured onto water and extracted with diethyl ether, the organic phase is dried over sodium sulphate and the solvent is distilled off in vacuo. The residue is stirred with diethyl ether and the crystals formed are filtered off. The solid is chromatographed over silica gel with diethylether/petroleum ether/methylene chloride (2:1:1). 0.9 g (40.8% of theory) of crystalline 2-({2-[(5,6-dihydro-[1,4,2]dioxazin-3-yl)-methoxyimino-methyl]-benzylidene}-hydrazono)-1-phenylpropan-1-one O-methyl oxime of melting point 136° C. is obtained.

Workup

  1. additionThe reaction mixture is poured onto water
  2. extractionextracted with diethyl ether
  3. dry with materialthe organic phase is dried over sodium sulphate
  4. distillationthe solvent is distilled off in vacuo
  5. customthe crystals formed
  6. filtrationare filtered off
  7. customThe solid is chromatographed over silica gel with diethylether/petroleum ether/methylene chloride (2:1:1)

Sources & evidence

ORD record
ord-a385d8404f66438298dafa7c5595ac41
Source dataset
uspto-grants-2002_07
Patent number
US06420362B1

Reaction notes

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