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

HRID 1845734Notes

Reaction equation

HRID 1845734 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-88ec2d14d9284f4494beb16071735fc0
Source dataset
uspto-grants-2015_02
Patent number
US08951536B2

Reaction notes

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