P-Anisidine → HCID 178492212, compound

HRID 1462199Notes

Reaction equation

HRID 1462199 reaction equation
[O:1]1[CH2:6][C:5](=O)[NH:4][C:3](=[O:8])[NH:2]1.[CH3:9][O:10][C:11]1[CH:17]=[CH:16][C:14]([NH2:15])=[CH:13][CH:12]=1.C[Si](C)(C)N[Si](C)(C)C>S([O-])([O-])(=O)=O.[NH4+].[NH4+].O1CCOCC1>[CH3:9][O:10][C:11]1[CH:17]=[CH:16][C:14]([NH:15][C:5]2[CH2:6][O:1][NH:2][C:3](=[O:8])[N:4]=2)=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 7732P-AnisidineHCID 13838HexamethyldisilazaneHCID 642154HCID 642154, compound

Product 1

HCID 178492212HCID 178492212, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 6097028Ammonium SulfateCatalystHCID 312751,4-DioxaneSolvent

Procedure

A solution of 1.16 g (0.010 mole) of 6H-1,2,4-oxadiazin-3,5(2H,4H)-dione, 5 mg ammonium sulfate, 1.47 g (0.012 mole) of p-methoxyaniline and 20 ml hexamethyldisilazane in 40 ml of freshly distilled dry dioxane is refluxed for 17 hours. After cooling, the dioxane and hexamethyldisilazane are removed in vacuo and the syrupy residue is dried on a vacuum pump for 2 hours. The resulting semi-solid residue is triturated with 100 ml of petroleum ether and filtered to give a yield of 1.3 g (59 percent) of 5-((4-methoxyphenyl)amino)-6H-1,2,4-oxadiazin-3(2H)-one.

Workup

  1. temperatureis refluxed for 17 hours
  2. temperatureAfter cooling
  3. customthe dioxane and hexamethyldisilazane are removed in vacuo
  4. customthe syrupy residue is dried on a vacuum pump for 2 hours
  5. customThe resulting semi-solid residue is triturated with 100 ml of petroleum ether
  6. filtrationfiltered

Sources & evidence

ORD record
ord-e4a9ec64bdfa495cb6bfa9a8bf30333b
Source dataset
uspto-grants-1984_07
Patent number
US04459403

Reaction notes

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