1,4-Dioxane → Ethyl 5-hydroxy-1,2,4-oxadiazole-3-carboxylate

HRID 2384106Notes

Reaction equation

HRID 2384106 reaction equation
[OH:1][NH:2][C:3](=[NH:9])[C:4]([O:6][CH2:7][CH3:8])=[O:5].C1CCN2C(=NCCC2)CC1.[O:21]1CCOC[CH2:22]1>>[O:21]=[C:22]1[O:1][N:2]=[C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[NH:9]1

Participants

4

Reactant 3

HCID 312751,4-DioxaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 178472862HCID 178472862, compound

Product 1

HCID 135973140Ethyl 5-hydroxy-1,2,4-oxadiazole-3-carboxylate

Conditions

Temperature
80 °C

Procedure

To a solution of ethyl 2-(hydroxyamino)-2-iminoacetate (2 g, 15.14 mmol) in dioxane (15.00 mL) is added CDl (2.7 g, 16.65 mmol) and DBU (2.5 ml, 16.65 mmol) at room temperature. After stirring for 1 hour at 80° C., the reaction is quenched with 1N HCl, and the crude is diluted with EtOAc. The organic layer is washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure to give ethyl 5-oxo-4,5-dihydro-1,2,4-oxadiazole-3-carboxylate (2.4 g). HPLC retention time=0.72 minutes (condition B); MS 159.1 (M+1).

Workup

  1. customthe reaction is quenched with 1N HCl
  2. additionthe crude is diluted with EtOAc
  3. washThe organic layer is washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ff9e2b1bb1f74f31a91ed12032b2f11a
Source dataset
uspto-grants-2012_09
Patent number
US08263629B2

Reaction notes

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