Methane → 5-(Benzyloxy)-7-[ethoxy(hydroxy)acetyl]-1,3-benzoxazol-2(3H)-one

HRID 33376Notes

Reaction equation

HRID 33376 reaction equation
[C:1]([C:4]1[C:12]2[O:11][C:10](=[O:13])[NH:9][C:8]=2[CH:7]=[C:6]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:5]=1)(=[O:3])[CH3:2].[Se](=O)=[O:23].C.[O:26]1CCO[CH2:28][CH2:27]1>O>[CH2:15]([O:14][C:6]1[CH:5]=[C:4]([C:1](=[O:3])[CH:2]([O:26][CH2:27][CH3:28])[OH:23])[C:12]2[O:11][C:10](=[O:13])[NH:9][C:8]=2[CH:7]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 297MethaneHCID 24007Selenium DioxideHCID 312751,4-DioxaneHCID 210728587-Acetyl-5-(benzyloxy)-1,3-benzoxazol-2(3H)-one

Product 1

HCID 210728515-(Benzyloxy)-7-[ethoxy(hydroxy)acetyl]-1,3-benzoxazol-2(3H)-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

20 g (71 mmol) 7-acetyl-5-benzyloxy-3H-benzoxazol-2-one and 8 g (72 mmol) selenium dioxide are refluxed for 8 hours in the presence of activated charcoal in 100 mL dioxane and 3.1 mL water. The solid is filtered off, the solvent is distilled off and the residue is combined with 50 mL ethanol. The mixture is refluxed for 15 minutes and then filtered through activated charcoal. The solid precipitated on cooling is suction filtered after 3 hours and washed with ethanol and diethyl ether.

Workup

  1. filtrationThe solid is filtered off
  2. distillationthe solvent is distilled off
  3. temperatureThe mixture is refluxed for 15 minutes
  4. filtrationfiltered through activated charcoal
  5. customThe solid precipitated
  6. temperatureon cooling
  7. filtrationis suction filtered after 3 hours
  8. washwashed with ethanol and diethyl ether

Sources & evidence

ORD record
ord-84c88a4e7743428886811c5169da4e36
Source dataset
uspto-grants-2008_09
Patent number
US07429583B2

Reaction notes

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