Sodium Hydroxide → HCID 20185725, compound

HRID 2052009Notes

Reaction equation

HRID 2052009 reaction equation
[O:1]([CH2:8][C:9](Cl)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:12][NH:13][CH2:14][CH2:15][CH2:16][P:17](=[O:20])([OH:19])[OH:18].[OH-].[Na+]>CC(C)=O>[OH:12][N:13]([CH2:14][CH2:15][CH2:16][P:17](=[O:18])([OH:20])[OH:19])[C:9](=[O:10])[CH2:8][O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 14798Sodium Hydroxide2×HCID 69703Phenoxyacetyl chlorideHCID 3421703-(Hydroxyamino)propylphosphonic acid

Product 1

HCID 20185725HCID 20185725, compoundYield 3.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A solution of phenoxyacetyl chloride (3.4 g.) in dried acetone (10 ml.) was added dropwise to a solution of 3-(N-hydroxyamino)propylphosphonic acid (1.51 g.) in mixture of 1 N aqueous sodium hydroxide solution (30 ml.) and acetone (20 ml.) under ice-cooling in the course of 10 minutes, and the mixture was stirred for an hour at the same temperature, and then adjusted to pH 10 with 1 N aqueous sodium hydroxide solution. The acetone was distilled off from the reaction mixture, and the remaining aqueous solution was adjusted to pH 2.0 with 10% hydrochloric acid, washed with ethyl ether, and then adjusted to pH 1.0 with 10% hydrochloric acid and saturated with sodium chloride. This solution was extracted twice with ethyl acetate (each 100 ml. portion) (insoluble materials (0.2 g.) produced at this stage were collected by filtration) and the combined extracts were dried over magnesium sulfate and evaporated to dryness under reduced pressure to give 3-(N-hydroxy-N-phenoxyacetylamino)propylphosphonic acid (0.1 g.). Insoluble materials produced above were identified with the same object compound.

Workup

  1. temperaturecooling in the course of 10 minutes
  2. distillationThe acetone was distilled off from the reaction mixture
  3. washwashed with ethyl ether
  4. extractionThis solution was extracted twice with ethyl acetate (each 100 ml
  5. customportion) (insoluble materials (0.2 g.) produced at this stage
  6. filtrationwere collected by filtration) and the combined extracts
  7. dry with materialwere dried over magnesium sulfate
  8. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-f7399f8d677a488c804ee2b3b4d78b70
Source dataset
uspto-grants-1980_01
Patent number
US04182758

Reaction notes

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