Diphosgene → 5-(2-nitrophenyl)-3H-1,3,4-oxadiazol-2-one

HRID 378967

Reaction equation

HRID 378967 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[CH:10][C:5]=1[C:6]([NH:8][NH2:9])=[O:7])([O-:3])=[O:2].Cl[C:15](OC(Cl)(Cl)Cl)=[O:16]>O1CCOCC1>[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[CH:10][C:5]=1[C:6]1[O:7][C:15](=[O:16])[NH:9][N:8]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 10426DiphosgeneHCID 3781218o-Nitrobenzohydrazide

Product 1

HCID 3129215-(2-nitrophenyl)-3H-1,3,4-oxadiazol-2-oneYield 86.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of 2-nitrobenzoylhydrazine (9.05 g, 0.05 mol) in dioxane (30 mL) was slowly added to a solution of trichloromethyl chloroformate (4.6 mL, 0.04 mol) in dioxane (30 mL) at room temperature. On completion of the addition the reaction was heated to reflux for 4 hours. The solvent was evaporated off and the residue re-crystallised from 96%. ethanol (50 mL) to give 7.15 g of the 5-(2-nitrophenyl)-3H-[1,3,4]oxadiazol -2-one. M.p. 157-158° C. A solution of the nitro compound (2 g, 9.7 mmol) in 96% ethanol (25 mL) was hydrogenated over 5% palladium on charcoal to give desired 1.6 g of the desired amine.

Workup

  1. additionOn completion of the addition the reaction
  2. temperaturewas heated
  3. temperatureto reflux for 4 hours
  4. customThe solvent was evaporated off
  5. customthe residue re-crystallised from 96%

Sources & evidence

ORD record
ord-0225d23dafec42378aeac7dae7b594a0
Source dataset
uspto-grants-2001_10
Patent number
US06297261B1

Linked notes

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