Thionyl Chloride → 4H,6H-furo(3,4-c)(1,2,5)oxadiazol-4-one

HRID 2097604Notes

Reaction equation

HRID 2097604 reaction equation
[O:1]1[CH2:5]/[C:4](=[N:6]\O)/[C:3](=[N:8]/[OH:9])/[C:2]1=[O:10].S(Cl)(Cl)=O>O1CCOCC1>[N:6]1[O:9][N:8]=[C:3]2[C:2](=[O:10])[O:1][CH2:5][C:4]=12

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 136361295(3Z,4Z)-3,4-bis(hydroxyimino)oxolan-2-one

Product 1

HCID 589417984H,6H-furo(3,4-c)(1,2,5)oxadiazol-4-one

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4H,6H-Furo[3,4-c][1,2,5]oxadiazol-4-one was synthesized according to literature procedures (Pollet, et al., Synthesis Communications, 1979, 977-979.) To a stirred solution of (3Z,4Z)-furan-2,3,4(5H)-trione 3,4-dioxime (3.0 g, 0.021 mol) in 1,4-dioxane (21 mL) under nitrogen, thionyl chloride (2.1 mL, 0.029 mol) was added dropwise. The resulting yellow solution was stirred overnight and then concentrated in vacuo. The resultant crystalline material was recrystallized once from a minimum amount of ethanol (EtOH) to give the desired compound as an off-white powder. The filtrate was concentrated down and recrystallized again. Combined solids yielded the desired product (2.0 g, 76%). 1H NMR (400 MHz, DMSO-d6) δ: 5.67 (s, 2H). MF═C4H2N2O3; LCMS calculated for C4H3N2O3(M+H)+: m/z=127.014.

Workup

  1. custom4H,6H-Furo[3,4-c][1,2,5]oxadiazol-4-one was synthesized
  2. concentrationconcentrated in vacuo
  3. customThe resultant crystalline material was recrystallized once from a minimum amount of ethanol (EtOH)

Sources & evidence

ORD record
ord-1bce5cb07a9f495fa57f58beb2c0c2b1
Source dataset
uspto-grants-2013_05
Patent number
US08450351B2

Reaction notes

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