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

HRID 722214

Reaction equation

HRID 722214 reaction equation
[C:1](Cl)(Cl)=[O:2].[CH3:5][O:6][C:7]1[CH:8]=[C:9]([CH:14]=[CH:15][C:16]=1[N+:17]([O-:19])=[O:18])[C:10]([NH:12][NH2:13])=[O:11]>C1(C)C=CC=CC=1.O1CCOCC1>[CH3:5][O:6][C:7]1[CH:8]=[C:9]([C:10]2[O:11][C:1](=[O:2])[NH:13][N:12]=2)[CH:14]=[CH:15][C:16]=1[N+:17]([O-:19])=[O:18]

Participants

5

Reactant 2

HCID 6371PhosgeneHCID 218838753-Methoxy-4-nitrobenzohydrazide

Product 1

HCID 218839065-(3-Methoxy-4-nitrophenyl)-1,3,4-oxadiazol-2(3H)-one

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 312751,4-DioxaneSolvent

Procedure

1.2 equivalents of a 20% phosgene solution in toluene were added dropwise to the solution of 850 mg of 3-methoxy-4-nitrobenzoic hydrazide (m.p.: 158.2° C., prepared from methyl 3-methoxy-4-nitrobenzoate and hydrazine hydrate in isopropanol at 80° C.) in 25 ml of dioxane and the mixture was stirred at room temperature for 1 hour. After concentrating, the residue was recrystallized from isopropanol, filtered off with suction and dried under reduced pressure.

Workup

  1. concentrationAfter concentrating
  2. customthe residue was recrystallized from isopropanol
  3. filtrationfiltered off with suction
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-2e7b460d44084e60b3df7a9aca359ce1
Source dataset
uspto-grants-2006_11
Patent number
US07138414B2

Linked notes

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