Water → 2-(3-oxo-3H-benzofuran-2-ylideneaminooxy)-ethyl acetate

HRID 1581817Notes

Reaction equation

HRID 1581817 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3](=[O:10])[C:2]1=[N:11][OH:12].C(=O)([O-])[O-].[Na+].[Na+].[C:19]([O:22][CH2:23][CH2:24]Br)(=[O:21])[CH3:20].O>CN1CCCC1=O>[C:19]([O:22][CH2:23][CH2:24][O:12][N:11]=[C:2]1[C:3](=[O:10])[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[O:1]1)(=[O:21])[CH3:20]

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 135641-Acetoxy-2-bromoethaneHCID 178516824HCID 178516824, compound

Product 1

HCID 543393342-(3-oxo-3H-benzofuran-2-ylideneaminooxy)-ethyl acetateYield 63%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

1.63 g (0.01 mol) of benzofuran-2,3-dione 2-oxime (XI-1) in 5 ml of N-methyl-2-pyrrolidinone are stirred with 1.14 g (0.0108 mol) of sodium carbonate at 20° C. for 30 minutes. After the addition of 1.7 g (0.0102 mol) of 2-bromoethyl acetate, stirring is continued at 70° C. for 2 hours. The mixture is poured into 30 ml of water and the product is filtered off. The product is dried to afford 1.57 g (63% of theory) of crystalline 2-(3-oxo-3H-benzofuran-2-ylideneaminooxy)-ethyl acetate (XIV-1).

Workup

  1. filtrationthe product is filtered off
  2. customThe product is dried

Sources & evidence

ORD record
ord-507b993bd68c4742afb97b836072224d
Source dataset
uspto-grants-2004_05
Patent number
US06730799B2

Reaction notes

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