Triphenylphosphine → HCID 23031297, compound

HRID 1269421Notes

Reaction equation

HRID 1269421 reaction equation
[I-:1].[NH:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[CH2:7][N+](C)(C)C.[C:12]1([P:18]([C:25]2C=CC=CC=2)[C:19]2C=CC=CC=2)C=CC=CC=1>C(#N)C>[I-:1].[NH:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[CH2:7][P+:18]([CH3:25])([CH3:19])[CH3:12]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 139751381H-Pyrrole-2-methanaminium, N,N,N-trimethyl-, iodide (1:1)

Product 1

HCID 23031297HCID 23031297, compoundYield 152.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Subsequently, to a suspension of (pyrrol-2-yl)methyl trimethylammonium iodide (7.59 g, 28.52 mmol) obtained above in acetonitrile (60 ml) was added triphenylphosphine (8.98 g, 34.2 mmol) with stirring, and the resulting mixture was stirred at 80° C. for 6 hours. After cooling, the reaction mixture was concentrated to about one-half of its initial volume, to which was added ethyl acetate (100 ml). The crystals precipitated were collected by filtration, washed with ethyl acetate and dried in vacuo to afford (pyrrol-2-yl)methyl trimethylphosphonium iodide (12.33 g, yield: 92%).

Workup

  1. stirringthe resulting mixture was stirred at 80° C. for 6 hours
  2. temperatureAfter cooling
  3. concentrationthe reaction mixture was concentrated to about one-half of its initial volume
  4. additionto which was added ethyl acetate (100 ml)
  5. customThe crystals precipitated
  6. filtrationwere collected by filtration
  7. washwashed with ethyl acetate
  8. customdried in vacuo

Sources & evidence

ORD record
ord-69096e8bd7294c3bb13089ea8e4bb274
Source dataset
uspto-grants-2007_04
Patent number
US07199150B2

Reaction notes

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