Acetic Acid → 3-(4-Chloro-3-hydroxyamino-2-methylbenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil

HRID 366342Notes

Reaction equation

HRID 366342 reaction equation
C(O)(=O)C.C(OCC)(=O)C.[Cl:11][C:12]1[C:17]2[C:18]([N+:22]([O-])=[O:23])=[C:19]([CH3:21])[O:20][C:16]=2[C:15]([N:25]2[C:30](=[O:31])[CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[N:27]([CH3:36])[C:26]2=[O:37])=[CH:14][CH:13]=1>[Fe].O>[Cl:11][C:12]1[C:17]2[C:18]([NH:22][OH:23])=[C:19]([CH3:21])[O:20][C:16]=2[C:15]([N:25]2[C:30](=[O:31])[CH:29]=[C:28]([C:32]([F:34])([F:35])[F:33])[N:27]([CH3:36])[C:26]2=[O:37])=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 8857Ethyl AcetateHCID 232891773-(4-Chloro-2-methyl-3-nitrobenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil

Product 1

HCID 232891843-(4-Chloro-3-hydroxyamino-2-methylbenzofuran-7-yl)-1-methyl-6-trifluoromethyluracilYield 54%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

5 ml of acetic acid, 200 ml of ethyl acetate and 100 ml of water were added to 2.3 g (5.7 mmol) of 3-(4-chloro-2-methyl-3-nitrobenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil and 1.6 g (28 mmol) of iron powder, followed by stirring for 2 hours under heating and refluxing. After completion of the reaction, insoluble matters were filtered off. The organic layer was washed sequentially with water and a sodium chloride aqueous solution and then, dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. Then, the obtained residue was purified by silica gel column chromatography to obtain 1.2 g (yield: 54%) of the desired product as pale yellow crystals. Melting point: 134-136° C.

Workup

  1. temperatureunder heating
  2. temperaturerefluxing
  3. customAfter completion of the reaction, insoluble matters
  4. filtrationwere filtered off
  5. washThe organic layer was washed sequentially with water
  6. dry with materiala sodium chloride aqueous solution and then, dried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customThen, the obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-1dee67ba238445768955cd7903a44206
Source dataset
uspto-grants-2000_10
Patent number
US06130187

Reaction notes

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