Ammonia → HCID 178527015, compound

HRID 1387922Notes

Reaction equation

HRID 1387922 reaction equation
[CH2:1]([PH2:8]=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:10]([O-])([OH:12])=[O:11].S(=O)(=O)(O)O.N>>[N+:10]([C:5]1[CH:6]=[CH:7][C:2]([CH2:1][PH2:8]=[O:9])=[CH:3][CH:4]=1)([O-:12])=[O:11]

Participants

5

Reactant 4

HCID 222AmmoniaHCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 178527014HCID 178527014, compound

Product 1

HCID 178527015HCID 178527015, compound

Conditions

Temperature
55 °C

Procedure

To 1-benzylphosphorane-1-oxide (4.17 g) were added nitric acid (1.7 ml) and sulfuric acid (11 ml) at 0° C., and the mixture was stirred at 50-60° C. for 2 hours. The reaction mixture was added to crushed ice and neutralized with ammonia solution. The mixture was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried with magnesium sulfate and concentrated. Under reduced pressure, The residue was separated and purified with column chromatography (ethanol/ethyl acetate=1:4→1:1) to give 1-(4-nitro-benzyl)phosphorane-1-oxide (2.22 g) as yellow crystals.

Workup

  1. additionThe reaction mixture was added
  2. customto crushed ice
  3. extractionThe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated sodium chloride solution
  5. dry with materialdried with magnesium sulfate
  6. concentrationconcentrated
  7. customUnder reduced pressure, The residue was separated
  8. custompurified with column chromatography (ethanol/ethyl acetate=1:4→1:1)

Sources & evidence

ORD record
ord-e4a2a3f0976f4c97b3d3f99a1eb5f6d5
Source dataset
uspto-grants-2001_07
Patent number
US06268354B1

Reaction notes

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