Water → HCID 10896897, compound

HRID 1596093Notes

Reaction equation

HRID 1596093 reaction equation
F[C:2]1[C:15]2[C:6](=[CH:7][C:8]3[C:13]([N:14]=2)=[C:12](F)[CH:11]=[CH:10][CH:9]=3)[CH:5]=[CH:4][CH:3]=1.[CH:17]1[CH:22]=[CH:21][C:20]([P-:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:19][CH:18]=1.[K+].O>O1CCOCC1.O1CCCC1>[C:24]1([P:23]([C:20]2[CH:21]=[CH:22][CH:17]=[CH:18][CH:19]=2)[C:2]2[C:15]3[C:6](=[CH:7][C:8]4[C:13]([N:14]=3)=[C:12]([P:23]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:20]3[CH:21]=[CH:22][CH:17]=[CH:18][CH:19]=3)[CH:11]=[CH:10][CH:9]=4)[CH:5]=[CH:4][CH:3]=2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 3

HCID 962WaterHCID 11042360KPPh2HCID 11053044HCID 11053044, compound

Product 1

HCID 10896897HCID 10896897, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 0.51 g (2.37 mmol) of 4,5-difluoroacridine (XIII) in 50 ml of 1,4-dioxane was added dropwise 9.3 ml (4.65 mmol) of a 0.5 M solution of potassium diphenylphosphide (Ph2P−K+) in tetrahydrofuran at room temperature. After the addition was completed, the mixture was heated at reflux for one hour. After cooling, 30 ml of distilled water was added to the brown reaction solution. The resulting precipitate was filtered off, washed thoroughly with distilled water, ethanol and n-pentane, and dried under high vacuum to obtain 1.02 g (79% of theory) of 4,5-bis(diphenylphosphino)acridine (Ia) as a yellow powder which will decompose from 255° C.

Workup

  1. additionAfter the addition
  2. temperaturethe mixture was heated
  3. temperatureat reflux for one hour
  4. temperatureAfter cooling
  5. filtrationThe resulting precipitate was filtered off
  6. washwashed thoroughly with distilled water, ethanol and n-pentane
  7. customdried under high vacuum

Sources & evidence

ORD record
ord-48c71a4406a745059aa25c8a1d49ae3e
Source dataset
uspto-grants-2001_09
Patent number
US06290926B1

Reaction notes

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