2,5-Hexanedione → 5-Methoxy-3-(4-(2,5-dimethylpyrrol-1-yl)-3-methylphenyl)-3H-(1,3,4)oxadiazol-2-one

HRID 840733Notes

Reaction equation

HRID 840733 reaction equation
[CH3:1][O:2][C:3]1[O:7][C:6](=[O:8])[N:5]([C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[C:11]([CH3:16])[CH:10]=2)[N:4]=1.[CH2:17]([CH2:21][C:22](=O)[CH3:23])[C:18]([CH3:20])=O>C(O)(=O)C>[CH3:1][O:2][C:3]1[O:7][C:6](=[O:8])[N:5]([C:9]2[CH:14]=[CH:13][C:12]([N:15]3[C:22]([CH3:23])=[CH:21][CH:17]=[C:18]3[CH3:20])=[C:11]([CH3:16])[CH:10]=2)[N:4]=1

Participants

4

Reactant 2

HCID 80352,5-HexanedioneHCID 98778575-methoxy-3-(4-amino-3-methylphenyl)-3H-(1,3,4)-oxadiazol-2-one

Product 1

HCID 226202695-Methoxy-3-(4-(2,5-dimethylpyrrol-1-yl)-3-methylphenyl)-3H-(1,3,4)oxadiazol-2-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The latter compound was obtained by reacting 5-methoxy-3-(4-amino-3-methylphenyl)-3H-(1,3,4)oxadiazol-2-one with equimolar amounts of acetonylacetone in glacial acetic acid at 80° C. Working up took place by dilution with water, extraction by shaking with ethyl acetate and column chromatography (silica gel, methylene chloride) of the crude product obtained after concentration of the dried organic phase.

Workup

  1. customThe latter compound was obtained
  2. customat 80° C
  3. extractionwith water, extraction
  4. customobtained after concentration of the dried organic phase

Sources & evidence

ORD record
ord-bc612ec0b78b4d84ba0b145a1cb527b2
Source dataset
uspto-grants-2002_04
Patent number
US06369088B2

Reaction notes

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