Ammonia → HCID 18472377, compound

HRID 565987Notes

Reaction equation

HRID 565987 reaction equation
[N+:1]([O-:4])(O)=[O:2].S(=O)(=O)(O)O.[CH2:10]([P:17](=[O:24])([CH2:21][CH2:22][CH3:23])[CH2:18][CH2:19][CH3:20])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.N>>[N+:1]([C:14]1[CH:15]=[CH:16][C:11]([CH2:10][P:17](=[O:24])([CH2:18][CH2:19][CH3:20])[CH2:21][CH2:22][CH3:23])=[CH:12][CH:13]=1)([O-:4])=[O:2]

Participants

5

Reactant 4

HCID 222AmmoniaHCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 15446537HCID 15446537, compound

Product 1

HCID 18472377HCID 18472377, compound

Conditions

Temperature
60 °C

Procedure

To a mixture of nitric acid (3.6 ml) and concentrated sulfuric acid (22 ml) was added benzyldipropylphosphineoxide (10.75 g) at 0° C., and the mixture was stirred at 60° C. for 1.5 hours. The reaction mixture was added to ice-water, and ammonia solution was added to the mixture to neutralize the solution, which was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried with magnesium sulfate and concentrated. The residue was separated and purified with column chromatography (ethyl acetate/ethanol=9:1→4:1) to give 4-nitrobenzyldipropylphosphine oxide (3.77 g) as pale yellow crystals.

Workup

  1. additionwas added to the mixture
  2. extractionwas extracted with ethyl acetate
  3. washThe organic layer was washed with saturated sodium chloride solution
  4. dry with materialdried with magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was separated
  7. custompurified with column chromatography (ethyl acetate/ethanol=9:1→4:1)

Sources & evidence

ORD record
ord-1deb204de4d64fd885df272bbfa7316f
Source dataset
uspto-grants-2001_01
Patent number
US06172061B2

Reaction notes

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