1,4-Dioxane → HCID 21951487, compound

HRID 1760352Notes

Reaction equation

HRID 1760352 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[C:6]([N+:14]([O-])=O)[C:5]=1[P:17](=[O:30])([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([O-])=O.O1CCOCC1>Cl>[NH2:14][C:6]1[CH:7]=[C:8]([C:10]([F:12])([F:13])[F:11])[CH:9]=[C:4]([NH2:1])[C:5]=1[P:17](=[O:30])([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 21951485HCID 21951485, compound

Product 1

HCID 21951487HCID 21951487, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
10 °C

Procedure

Into a 500 mL Erlenmeyer flask equipped with a stir bar was placed (2,6-dinitro-4-trifluoromethylphenyl)diphenylphosphine oxide (6.48 g, 0.0149 mol) and 1,4-dioxane (100 mL). The mixture was cooled in an ice bath to ˜10° C. A solution of stannous chloride dihydrate (31.22 g, 0.1384 mol) in concentrated hydrochloric acid (130 mL) was added dropwise over ˜1 hour. Once the addition was complete, the mixture was allowed to warm to room temperature with stirring. After ˜16 hours, the crude amine salt was collected via filtration, added to ice water and basified to a pH of ˜10 with ammonium hydroxide. The crude solid was isolated by filtration, washed with water, and air dried at room temperature to afford 5.11 g (91% crude yield) of a white powder. The solid exhibited a sharp endothermic peak at 172° C. as determined by differential scanning calorimetry (DSC) at a heating rate of 10° C./min. Recrystallization from ˜50% aqueous ethanol afforded tan plates (3.86 g, 69% yield) exhibiting a sharp endothermic peak at 174.17° C. by DSC.

Workup

  1. customInto a 500 mL Erlenmeyer flask equipped with a stir bar
  2. additionOnce the addition
  3. temperatureto warm to room temperature
  4. filtrationthe crude amine salt was collected via filtration
  5. additionadded to ice water
  6. customThe crude solid was isolated by filtration
  7. washwashed with water, and air
  8. customdried at room temperature
  9. customto afford 5.11 g (91% crude yield) of a white powder
  10. customat 172° C.
  11. customRecrystallization from ˜50% aqueous ethanol afforded tan plates (3.86 g, 69% yield)
  12. customat 174.17° C.

Sources & evidence

ORD record
ord-44a226dff14047969c1545b5832045d5
Source dataset
uspto-grants-2005_01
Patent number
US06841652B2

Reaction notes

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