Methanol → Diethyl 3-(N-Hydroxyamino)propylphosphate

HRID 2051974Notes

Reaction equation

HRID 2051974 reaction equation
Cl.[NH2:2][OH:3].[OH-].[Na+].CO.Br[CH2:9][CH2:10][CH2:11][P:12](=[O:19])([O:16][CH2:17][CH3:18])[O:13][CH2:14][CH3:15]>O>[OH:3][NH:2][CH2:9][CH2:10][CH2:11][P:12](=[O:19])([O:16][CH2:17][CH3:18])[O:13][CH2:14][CH3:15]

Participants

6

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 283500Diethyl (3-bromopropyl)phosphonateHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 9794336Diethyl 3-(N-Hydroxyamino)propylphosphateYield 62.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of hydroxylamine hydrochloride (55.6 g.) in water (100 ml.) were added solution of sodium hydroxide (32.0 g.) in water (75 ml.) under ice-cooling and then methanol (75 ml.). To this solution was added dropwise diethyl 3-bromopropylphosphonate (25.5 g.), whereafter the mixture was warmed at 40°-45° C. for 3 hours with stirring. The methanol was distilled off under reduced pressure. The resultant aqueous solution was adjusted to pH 8 with sodium bicarbonate, washed three times with benzene which were discarded (once with 150 ml. and twice with 100 ml. portions) and then extracted with three 150 ml. portions of chloroform. The chloroform extracts were combined, dried over magnesium sulfate and evaporated to dryness under reduced pressure to give oily diethyl 3-(N-hydroxyamino)propylphosphonate (13.05 g.).

Workup

  1. temperaturecooling
  2. temperaturewhereafter the mixture was warmed at 40°-45° C. for 3 hours
  3. distillationThe methanol was distilled off under reduced pressure
  4. washwashed three times with benzene which
  5. extractionportions) and then extracted with three 150 ml
  6. dry with materialdried over magnesium sulfate
  7. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-dc562a495836489e9528b00349a169dc
Source dataset
uspto-grants-1980_01
Patent number
US04182758

Reaction notes

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