Ethanol → Ethyl 4-amino-1,2,5-oxadiazole-3-carboxylate

HRID 1371558Notes

Reaction equation

HRID 1371558 reaction equation
[NH2:1][C:2]1[C:3]([C:7]([OH:9])=[O:8])=[N:4][O:5][N:6]=1.O=S(Cl)Cl.[CH3:14][CH2:15]O>>[NH2:1][C:2]1[C:3]([C:7]([O:9][CH2:14][CH3:15])=[O:8])=[N:4][O:5][N:6]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 5474544-Amino-1,2,5-oxadiazole-3-carboxylic acid

Product 1

HCID 1244576Ethyl 4-amino-1,2,5-oxadiazole-3-carboxylateYield 50%

Procedure

To a solution of 4-amino-1,2,5-oxadiazole-3-carboxylic acid (0.25 g, 1.9 mmol) in 2 mL of EtOH was added SOCl2 (0.2 mL) dropwise, under cooling with an ice-bath. The resulting mixture was refluxed for 4 hours and then concentrated. The oil was diluted with 50 mL of H2O and extracted with diethyl ether (3×100 mL). The combined organic layer was dried over MgSO4 and concentrated to give a white solid (0.15 g, 50%). 1H NMR (DMSO, 500 MHz) δ 6.39 (s, 2H), 4.39 (q, 2H), 1.35 (t, 3H). Mass Spec. FIA MS 158.1 (M+1).

Workup

  1. temperatureunder cooling with an ice-bath
  2. temperatureThe resulting mixture was refluxed for 4 hours
  3. concentrationconcentrated
  4. additionThe oil was diluted with 50 mL of H2O
  5. extractionextracted with diethyl ether (3×100 mL)
  6. dry with materialThe combined organic layer was dried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-7b823a1b36ea4c6b91aedc5a5deb3668
Source dataset
uspto-grants-2007_01
Patent number
US07157476B2

Reaction notes

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