Dichloromethane → HCID 10896897, compound

HRID 1596094Notes

Reaction equation

HRID 1596094 reaction equation
Br[C:2]1[C:15]2[C:6](=[CH:7][C:8]3[C:13]([N:14]=2)=[C:12](Br)[CH:11]=[CH:10][CH:9]=3)[CH:5]=[CH:4][CH:3]=1.Cl[P:18]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[Mg].ClCCl>O1CCCC1.ClCCl.CCCCCC>[C:19]1([P:18]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:2]2[C:15]3[C:6](=[CH:7][C:8]4[C:13]([N:14]=3)=[C:12]([P:18]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:11]=[CH:10][CH:9]=4)[CH:5]=[CH:4][CH:3]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 66180ChlorodiphenylphosphineHCID 6307804,5-DibromoacridineHCID 5462224Magnesium

Product 1

HCID 10896897HCID 10896897, compoundYield 15%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 21226440Methylenechloride HexaneSolvent

Procedure

A solution of 337 mg (1 mmol) of 4,5-dibromoacridine (XIX) and 440 mg (2 mmol) of chlorodiphenylphosphane (Ph2PCl) in 40 ml of tetrahydrofuran was added dropwise to a boiling suspension of 72 mg (3 mmol) of magnesium powder in 20 ml of tetrahydrofuran. The mixture was then stirred at room temperature for 20 h. Hydrolysis with water and diluted hydrochlorid acid, extraction with diethyl ether, drying the ether phase over sodium sulfate and distilling off the solvent gave a brown raw product, from which 72 mg (15% of theory) of 4,5-bis(diphenylphosphino)acridine (Ia) was obtained as a yellow powder by several recrystallizations from dichloromethane and dichloromethane/hexane.

Workup

  1. customHydrolysis
  2. extractionwith water and diluted hydrochlorid acid, extraction with diethyl ether
  3. dry with materialdrying the ether phase over sodium sulfate
  4. distillationdistilling off the solvent
  5. customgave a brown raw product

Sources & evidence

ORD record
ord-821f8e79ca87410d9b83477cb1f74270
Source dataset
uspto-grants-2001_09
Patent number
US06290926B1

Reaction notes

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