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

HRID 2212059Notes

Reaction equation

HRID 2212059 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-ffbf31cdefe945a6a4356996fc0b5782
Source dataset
uspto-grants-2006_09
Patent number
US07101900B2

Reaction notes

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