Ethanol → Ethyl 2,1,3-benzoxadiazole-5-carboxylate

HRID 655434Notes

Reaction equation

HRID 655434 reaction equation
[N:1]1[O:2][N:3]=[C:4]2[CH:9]=[C:8]([C:10]#N)[CH:7]=[CH:6][C:5]=12.[OH:12]S(O)(=O)=O.[CH3:17][CH2:18][OH:19]>>[N:1]1[O:2][N:3]=[C:4]2[CH:9]=[C:8]([C:10]([O:19][CH2:18][CH3:17])=[O:12])[CH:7]=[CH:6][C:5]=12

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 27354522,1,3-Benzoxadiazole-5-carbonitrile

Product 1

HCID 2736368Ethyl 2,1,3-benzoxadiazole-5-carboxylateYield 75%

Procedure

To a solution of benzo[c][1,2,5]oxadiazole-5-carbonitrile (700 mg, 1.33 mol) in EtOH (100 mL) was added H2SO4 (20 mL) and the reaction mixture was refluxed for 14 h. The reaction was concentrated in vacuo and the residue was diluted with water (50 mL), and extracted with DCM (2×100 mL). The combined organic layers were dried over magnesium sulfate, filtered, and then concentrated in vacuo to afford ethyl benzo[c][1,2,5]oxadiazole-5-carboxylate (0.7 g, 75%) as a yellow, sticky solid.

Workup

  1. temperaturethe reaction mixture was refluxed for 14 h
  2. concentrationThe reaction was concentrated in vacuo
  3. additionthe residue was diluted with water (50 mL)
  4. extractionextracted with DCM (2×100 mL)
  5. dry with materialThe combined organic layers were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0851decbf47b413ab11b58da53d64004
Source dataset
uspto-grants-2011_12
Patent number
US08071595B2

Reaction notes

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