Hydrochloric Acid → HCID 178521499, compound

HRID 1581823Notes

Reaction equation

HRID 1581823 reaction equation
C([O:4][CH2:5][CH2:6][O:7][N:8]=[C:9]1[C:13](=[N:14][OH:15])[C:12]2[CH:16]=[CH:17][CH:18]=[CH:19][C:11]=2[O:10]1)(=O)C.[OH-].[Na+].Cl>CN(C)C=O>[OH:4][CH2:5][CH2:6][O:7][N:8]=[C:9]1[C:13](=[N:14][OH:15])[C:12]2[CH:16]=[CH:17][CH:18]=[CH:19][C:11]=2[O:10]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 178476495HCID 178476495, compound

Product 1

HCID 178521499HCID 178521499, compoundYield 31.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

At 20° C., 5.28 g (0.02 mol) of 2-(3-hydroxyimino-3H-benzofuran-2-ylideneaminooxy)-ethyl acetate (XVI-1) in 20 ml of dimethylformamide are stirred with 4.24 g (0.048 mol) of 45% strength aqueous sodium hydroxide solution for 3 hours. The mixture is acidified with 2 N hydrochloric acid and extracted with ethyl acetate, the organic phase is dried over sodium sulphate and the solvent is distilled off under reduced pressure. According to HPLC analysis, the crude product contains 23.4% of the stereoisomer A and 4.1% of the stereoisomer B of benzofuran-2,3-dione 2-[O-(2-hydroxy-ethyl)-oxime] 3-oxime (X-1). Stirring the crude product with diethyl ether affords 1.4 g (28.5% of theory) of crystalline benzofuran-2,3-dione 2-[O-(2-hydroxy-ethyl)-oxime] 3-oxime α-1) consisting of 84.7% of stereoisomer A and 6% of stereoisomer B (HPLC).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialthe organic phase is dried over sodium sulphate
  3. distillationthe solvent is distilled off under reduced pressure

Sources & evidence

ORD record
ord-42e3b7a8bfc642c19098bdc436548575
Source dataset
uspto-grants-2004_05
Patent number
US06730799B2

Reaction notes

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