Hydrochloric Acid → (E)-(5,6-dihydro-1,4,2-dioxazin-3-yl)(2-hydroxyphenyl)methanone O-methyloxime

HRID 1018123Notes

Reaction equation

HRID 1018123 reaction equation
[O:1]1[CH2:6][CH2:5][O:4][C:3](/[C:7](/[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[OH:16])=[N:8]\[OH:9])=[N:2]1.[C:17](=O)([O-])[O-].[Na+].[Na+].S(OC)(OC)(=O)=O.Cl>CN(C)C=O>[CH3:17][O:9]/[N:8]=[C:7](\[C:3]1[O:4][CH2:5][CH2:6][O:1][N:2]=1)/[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[OH:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6497Dimethyl SulfateHCID 10340Sodium CarbonateHCID 1357442132-[(Z)-C-(5,6-dihydro-1,4,2-dioxazin-3-yl)-N-hydroxycarbonimidoyl]phenol

Product 1

HCID 135512723(E)-(5,6-dihydro-1,4,2-dioxazin-3-yl)(2-hydroxyphenyl)methanone O-methyloximeYield 62.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.2 g (0.0054 mol) of Z-(5,6-dihydro-1,4,2-dioxazin-3-yl)-(2-hydroxy-phenyl)-methanone oxime (V-1) in 5 ml of dimethylformamide are stirred at 20° C. together with 0.66 g (0.0062 mol) of sodium carbonate initially for 30 minutes. 0.83 g (0.00658 mol) of dimethyl sulphate is then added and stirring is continued at 20° C. for a further 16 hours. The reaction mixture is adjusted to a slightly acidic pH using 2 N aqueous hydrochloric acid and extracted with ethyl acetate. The organic phase is dried over sodium sulphate and the solvent is distilled off under reduced pressure. 0.8 g (50.35% of theory) of Z-(5,6-dihydro-1,4,2-dioxazin-3-yl)-(2-hydroxy-phenyl)-methanone O-methyl-oxime (1) of a purity of 80.3% (HPLC) is obtained.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic phase is dried over sodium sulphate
  3. distillationthe solvent is distilled off under reduced pressure

Sources & evidence

ORD record
ord-ed10cbf0a86a4bed8b6d6532c112da9f
Source dataset
uspto-grants-2002_11
Patent number
US06479675B1

Reaction notes

Loading…