Aniline → Tetrakis(anilinomethyl)phosphanium chloride

HRID 1288097Notes

Reaction equation

HRID 1288097 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>C(O)C>[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 chloride

Product 1

HCID 21503996Tetrakis(anilinomethyl)phosphanium chlorideYield 93%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Aniline (7.70 g) was added to a solution of 3.83 g of tetrakis(hydroxymethyl)phosphonium chloride (THPC) in 75 ml of ethanol. There was a mild exotherm, followed immediately by the separation of solids. The mixture was stirred for 2 hours and then filtered, giving 9.15 g (93.0 percent yield) of tetrakis(anilinomethyl)phosphonium chloride, m.p. 129°-130°, as a white crystalline solid that yellowed rapidly on exposure to light. No further solids separated from the filtrate in the next 5 hours. The filtrate and washings, stripped under vacuum, left 1.15 g of a yellow oil containing the remainder of the product and the unreacted aniline.

Workup

  1. customfollowed immediately by the separation of solids
  2. filtrationfiltered

Sources & evidence

ORD record
ord-ca904fe396d64465a4a7e9021620c59b
Source dataset
uspto-grants-1976_10
Patent number
US03987098

Reaction notes

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