Ethanol → HCID 136109128, compound

HRID 1862357Notes

Reaction equation

HRID 1862357 reaction equation
[C:1]1(=[O:8])[CH2:6][CH2:5][CH2:4][C:3](=O)[CH2:2]1.[Br:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][C:17]=1[F:18])C=O.[NH2:19][C:20]1[CH:24]=[CH:23][NH:22][N:21]=1.[CH2:25](O)C>>[Br:9][C:10]1[CH:11]=[CH:12][C:15]([CH:25]2[C:2]3[C:1](=[O:8])[CH2:6][CH2:5][CH2:4][C:3]=3[NH:19][C:20]3=[CH:24][CH:23]=[N:22][N:21]23)=[CH:16][C:17]=1[F:18]

Participants

5

Reactant 4

HCID 702EthanolHCID 104341,3-CyclohexanedioneHCID 1736043-Bromo-4-fluorobenzaldehydeHCID 178418806HCID 178418806, compound

Product 1

HCID 136109128HCID 136109128, compoundYield 49%

Procedure

A solution of 1,3-cyclohexanedione (0.56 g, 5 mmol), 3-bromo-4-fluorobenzaldehyde (1.01 g, 5 mmol), and 3-aminopyrazole (0.41 g, 5 mmol) in ethanol (5 mL) was heated at reflux for 24 hours. After the reaction mixture was allowed to cool to ambient temperature, the volatiles were evaporated at reduced pressure and the resulting residue was chromatographed on silica gel, eluting with 5% ethanol/methylene chloride to provide 0.9 g (49%) of the title compound.

Workup

  1. temperatureat reflux for 24 hours
  2. customthe volatiles were evaporated at reduced pressure
  3. customthe resulting residue was chromatographed on silica gel
  4. washeluting with 5% ethanol/methylene chloride

Sources & evidence

ORD record
ord-58ee717588ac4981b78cfb3fdf7464bd
Source dataset
uspto-grants-2003_03
Patent number
US06538000B1

Reaction notes

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