Ammonia → HCID 18472377, compound

HRID 1387916Notes

Reaction equation

HRID 1387916 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 benzyldipropylphosphine-oxide (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-7dd51dbea6c84f4abbe69102dfdfc334
Source dataset
uspto-grants-2001_07
Patent number
US06268354B1

Reaction notes

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