Bis-(1H-imidazol-2-YL)-methanone → HCID 15017666, compound

HRID 1656909Notes

Reaction equation

HRID 1656909 reaction equation
[CH:1]([C:3]1[C:4]([F:14])=[C:5]([CH:9]=[C:10]([F:13])[C:11]=1[F:12])[C:6]([OH:8])=O)=[CH2:2].[C:15]([C:22]1NC=CN=1)(C1NC=CN=1)=[O:16].C([CH:29](C([O-])=O)[C:30]([O-])=[O:31])C.C(C(C([O-])=O)C([O-])=O)C.[Mg+2].[Mg+2]>Cl>[CH:1]([C:3]1[C:4]([F:14])=[C:5]([C:6](=[O:8])[CH2:29][C:30]([O:16][CH2:15][CH3:22])=[O:31])[CH:9]=[C:10]([F:13])[C:11]=1[F:12])=[CH2:2]

Participants

5

Reactant 3

HCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 15017665HCID 15017665, compoundHCID 19046054HCID 19046054, compound

Product 1

HCID 15017666HCID 15017666, compoundYield 93.7%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To a cooled solution (0° to 5° C.) of 3-ethenyl-2,4,5-trifluorobenzoic acid (6.0 g, 0.03 mol) (100 mL) was added carbonyl diimidazole (4.9 g, 0.030 mol). The mixture was then stirred at room temperature for 1 hour, heated with magnesium bis-(ethyl malonate) (8.7 g, 0.03 mol) and refluxed for 3 hours. The reaction was allowed to cool, treated with 3N HCl (30 mL) and stirred for 1.5 hours at room temperature. The reaction was partitioned between ether and water. The organic layer was dried and concentrated to provide 7.65 g (93%) of the desired product. An analytical sample was obtained by preparative TLC (SiOz, 9:1 hexane/EtOAC) Analysis Calcd: C 57.36, H 4.17, F 20.94;

Workup

  1. temperaturerefluxed for 3 hours
  2. temperatureto cool
  3. stirringstirred for 1.5 hours at room temperature
  4. customThe reaction was partitioned between ether and water
  5. customThe organic layer was dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-53d37bf67fc142e8a9ed62eeb250ae5f
Source dataset
uspto-grants-1993_10
Patent number
US05256662

Reaction notes

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