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

HRID 969447Notes

Reaction equation

HRID 969447 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 stirred in the presence of activated charcoal in 100 mL dioxane and 3.1 mL water for 8 hours at reflux temperature. 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 that precipitates on cooling is suction filtered for 3 hours and washed with ethanol and diethyl ether.

Workup

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

Sources & evidence

ORD record
ord-1dc5008e3017447abec781a37859da63
Source dataset
uspto-grants-2007_12
Patent number
US07307076B2

Reaction notes

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