Dimethylformamide → 5-Methoxy-3-(4-dimethylamino-3-methylphenyl)-3H-(1,3,4)-oxadiazol-2-one

HRID 840729Notes

Reaction equation

HRID 840729 reaction equation
COC1[O:7][C:6](=O)[N:5]([C:9]2[CH:14]=[CH:13][C:12](N)=[C:11](C)[CH:10]=2)[N:4]=1.[CH2:17]=O.[CH:19]([OH:21])=[O:20].[CH3:22][N:23]([CH:25]=O)[CH3:24]>>[CH3:17][O:20][C:19]1[O:21][C:6](=[O:7])[N:5]([C:9]2[CH:14]=[CH:13][C:25]([N:23]([CH3:22])[CH3:24])=[C:11]([CH3:12])[CH:10]=2)[N:4]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 98778575-methoxy-3-(4-amino-3-methylphenyl)-3H-(1,3,4)-oxadiazol-2-oneHCID 18761834Formaldehyde formic acid

Product 1

HCID 699699165-Methoxy-3-(4-dimethylamino-3-methylphenyl)-3H-(1,3,4)-oxadiazol-2-one

Procedure

The latter compound was obtained by reacting 5-methoxy-3-(4-amino-3-methylphenyl)-3H-(1,3,4)oxadiazol-2-one with paraformaldehyde/formic acid in DMF at room temperature and was purified by column chromatography (silica gel, ethyl acetate:n-heptane=1:1).

Workup

  1. customThe latter compound was obtained
  2. customat room temperature
  3. customwas purified by column chromatography (silica gel, ethyl acetate:n-heptane=1:1)

Sources & evidence

ORD record
ord-706d9578ab0547939b3e9a8f4354a098
Source dataset
uspto-grants-2002_04
Patent number
US06369088B2

Reaction notes

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