Aniline → Tetrakis(anilinomethyl)phosphanium chloride

HRID 1076073Notes

Reaction equation

HRID 1076073 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-:8].O[CH2:10][P+:11]([CH2:16]O)([CH2:14]O)[CH2:12]O>CC(C)=O>[Cl-:8].[NH:1]([CH2:10][P+:11]([CH2:16][NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)([CH2:14][NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:12][NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 31298Tetrakis(hydroxymethyl)phosphonium chloride2×

Product 1

HCID 21503996Tetrakis(anilinomethyl)phosphanium chlorideYield 66.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Aniline (9.30g) was added all at once to a slurry of 4.76 g of tetrakis(hydroxymethyl)phosphonium chloride (THPC) in 50 ml of acetone. The THPC dissolved within one minute, with slight warming, giving a clear solution that deposited solids on standing. After 2 hr, the mixture was filtered, giving 8.15 g (66.0% yield) of tetrakis(anilinomethyl)phosphonium chloride, m.p. 120°-121°. The filtrate, concentrated on a rotary evaporator, left 16.45 g of a neutral, dark yellow liquid. Beilstein tests on these products were strongly positive on the solid fraction and faintly positive on the liquid fraction, showing that most of the chlorine went into the solid fraction.

Workup

  1. customgiving a clear solution
  2. filtrationthe mixture was filtered

Sources & evidence

ORD record
ord-85276eff8bd94b2d86d73373cc8acba3
Source dataset
uspto-grants-1976_05
Patent number
US03954866

Reaction notes

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