Sodium Carbonate → 2-(2,6-Dichloro-phenyl)-N-hydroxy-acetamidine

HRID 1815748Notes

Reaction equation

HRID 1815748 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl: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]([Cl:8])[C:3]=1[CH2:9][C:10](=[N:13][OH:14])[NH2:11]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 76678(2,6-Dichlorophenyl)acetonitrileHCID 443297Hydroxyamine hydrochlorideHCID 23672064Monosodium phosphate

Product 1

HCID 27581642-(2,6-Dichloro-phenyl)-N-hydroxy-acetamidineYield 17.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

15.0 g (81 mmol) of (2,6-dichlorophenyl)acetonitrile in 60 ml of ethanol were admixed with 10.3 g (148 mmol) of hydroxylamine hydrochloride and then with 11.1 g (105 mmol) of sodium carbonate dissolved in 40 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. The resulting white solid precipitate (14.0 g) was filtered off and dried under reduced pressure. More product (3.1 g) was obtained from the extract after removal of the solvent under reduced pressure. The overall yield was 17.1 g, m.p. 172-173° C.

Workup

  1. temperatureThis mixture was refluxed for 4 h
  2. extractionextracted with methylene chloride
  3. filtrationThe resulting white solid precipitate (14.0 g) was filtered off
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-d093d55068524c4188ab4bfa91d4f7ec
Source dataset
uspto-grants-2005_04
Patent number
US06881742B1

Reaction notes

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