Aniline → Tetrakis(anilinomethyl)phosphanium chloride

HRID 1288098Notes

Reaction equation

HRID 1288098 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 (9.30 g) 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 1 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 percent 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-bb3a7d33e8bc4d99bed3c1a01396b194
Source dataset
uspto-grants-1976_10
Patent number
US03987098

Reaction notes

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