N'-[(3,4-dimethoxy-5-nitrobenzoyl)oxy]acetamidine → 5-(3,4-Dimethoxy-5-nitrophenyl)-3-methyl-1,2,4-oxadiazole

HRID 725416

Reaction equation

HRID 725416 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:13]=[C:14]([N+:18]([O-:20])=[O:19])[C:15]=1[O:16][CH3:17])[C:6]([O:8][N:9]=[C:10]([NH2:12])[CH3:11])=O>C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:6]2[O:8][N:9]=[C:10]([CH3:11])[N:12]=2)[CH:13]=[C:14]([N+:18]([O-:20])=[O:19])[C:15]=1[O:16][CH3:17]

Participants

3

Reactant 1

HCID 53789064N'-[(3,4-dimethoxy-5-nitrobenzoyl)oxy]acetamidine

Product 1

HCID 214590805-(3,4-Dimethoxy-5-nitrophenyl)-3-methyl-1,2,4-oxadiazole

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2.0 g of N'-[(3,4-dimethoxy-5-nitrobenzoyl)oxy]acetamidine are held at reflux temperature for 1 hour in 20 ml of glacial acetic acid. After distillation of the acetic acid, the crystalline residue is recrystallized from ether/hexane. There is obtained 5-(3,4-dimethoxy-5-nitrophenyl)-3-methyl-1,2,4-oxadiazole in the form of colorless crystals of m.p. 111°.

Workup

  1. distillationAfter distillation of the acetic acid
  2. customthe crystalline residue is recrystallized from ether/hexane

Sources & evidence

ORD record
ord-d89e00ebc313469ab2bb5c8241814ec0
Source dataset
uspto-grants-1998_01
Patent number
US05705703

Linked notes

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