Sodium Carbonate → (2-chloro-6-fluorophenyl)acetamidoxime

HRID 1815749Notes

Reaction equation

HRID 1815749 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[CH2:9][C:10]#[N:11].Cl.[NH2:13][OH:14].C(=O)([O-])[O-].[Na+].[Na+].P([O-])(O)(O)=O.[Na+]>C(O)C.O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[CH2:9][C:10](=[N:13][OH:14])[NH2:11]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 1235752-Chloro-6-fluorophenylacetonitrileHCID 443297Hydroxyamine hydrochlorideHCID 23672064Monosodium phosphate

Product 1

HCID 4518017(2-chloro-6-fluorophenyl)acetamidoximeYield 41%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

10.0 g (59 mmol) of (2-chloro-6-fluorophenyl)acetonitrile in 50 ml of ethanol were admixed with 7.0 g (101 mmol) of hydroxylamine hydrochloride and then with 7.5 g (71 mmol) of sodium carbonate dissolved in 30 ml of water. This mixture was refluxed for 4 h, poured into aqueous sodium dihydrogen phosphate buffer (pH 7.8) and extracted with methylene chloride, and the extract was dried over sodium sulfate. The solvent was removed under reduced pressure, and 4.9 g of product were obtained from the extract. A further 3.7 g precipitated from the aqueous phase. Overall yield: 8.6 g, which were directly reacted further.

Workup

  1. temperatureThis mixture was refluxed for 4 h
  2. extractionextracted with methylene chloride
  3. dry with materialthe extract was dried over sodium sulfate
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-acf0b7d663cc41dba49fd5e1a0ae783c
Source dataset
uspto-grants-2005_04
Patent number
US06881742B1

Reaction notes

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