Bis-(1H-imidazol-2-YL)-methanone → 6,7-Difluorobenzo[d]isoxazol-3(2h)-one

HRID 245527Notes

Reaction equation

HRID 245527 reaction equation
[F:1][C:2]1[C:3]([OH:13])=[C:4]([CH:9]=[CH:10][C:11]=1[F:12])[C:5]([NH:7]O)=[O:6].C(C1NC=CN=1)(C1NC=CN=1)=O>C1COCC1>[F:12][C:11]1[CH:10]=[CH:9][C:4]2[C:5](=[O:6])[NH:7][O:13][C:3]=2[C:2]=1[F:1]

Participants

4

Reactant 2

HCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 866581193,4-difluoro-N,2-dihydroxybenzamide2×

Product 1

HCID 569462386,7-Difluorobenzo[d]isoxazol-3(2h)-oneYield 96.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3,4-difluoro-N,2-dihydroxybenzamide (Intermediate 527, 7.91 g, 41.8 mmol) and carbonyl diimidazole (13.6 g, 83.7 mmol) in THF (200 ml) was heated at reflux for 90 min. The mixture was partitioned between EtOAC and water and acidified with conc. HCl. The solution was extracted 3 times with EtOAc, each extract being washed with water and brine. Drying (MgSO4) of the combined extracts and removal of solvent gave 6.88 g of product as an off-white solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 90 min
  3. customThe mixture was partitioned between EtOAC and water
  4. extractionThe solution was extracted 3 times with EtOAc
  5. washeach extract being washed with water and brine
  6. customDrying
  7. custom(MgSO4) of the combined extracts and removal of solvent

Sources & evidence

ORD record
ord-aaf2e4ebf62843d494d4dce2cd486492
Source dataset
uspto-grants-2014_02
Patent number
US08658641B2

Reaction notes

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