Sodium Hydroxide → HCID 53776389, compound

HRID 22298Notes

Reaction equation

HRID 22298 reaction equation
[Cl:1][C:2]1[C:3]([CH3:12])=[C:4]([CH:9]=[CH:10][CH:11]=1)[O:5][CH2:6][C:7]#[N:8].Cl.[NH2:14][OH:15].[OH-].[Na+]>C(O)C.O>[Cl:1][C:2]1[C:3]([CH3:12])=[C:4]([CH:9]=[CH:10][CH:11]=1)[O:5][CH2:6][C:7](=[N:14][OH:15])[NH2:8]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 22075474HCID 22075474, compound

Product 1

HCID 53776389HCID 53776389, compoundYield 90.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

29.2 g (160.7 mmol) of 3-chloro-2-methyl-phenoxyacetonitrile are added to a solution of 13.5 g (194.2 mmol) of hydroxylamine hydrochloride, 7.7 g (194.2 mmol) of sodium hydroxide in 265 ml of ethanol and 68 ml of water. The mixture is heated at reflux temperature until the reaction is complete (approximately 48 to 60 hours) and the entire batch is subsequently stirred into 250 ml of water. The solid which precipitates in this process is separated off, washed with a small amount of water and dried. 31.1 g (90.2% of theory) of 3-chloro-2-methylphenoxyacetamide oxime are obtained.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux temperature until the reaction
  3. custom(approximately 48 to 60 hours)
  4. customThe solid which precipitates in this process
  5. customis separated off
  6. washwashed with a small amount of water
  7. customdried

Sources & evidence

ORD record
ord-aa0f88f5567d4fcda3a90af48f11be4b
Source dataset
uspto-grants-1995_06
Patent number
US05428047

Reaction notes

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