Phosphonic acid → HCID 88799872, compound

HRID 971600Notes

Reaction equation

HRID 971600 reaction equation
[PH:1](=[O:4])([OH:3])[OH:2].ClCP(CCl)(=O)O.[C:12](N)([CH3:15])([CH3:14])[CH3:13].[C:17]([NH:21][CH2:22]P(CNC(C)(C)C)(=O)O)(C)(C)C>O>[C:12]([O:4][P:1]([CH2:17][NH:21][CH3:22])(=[O:3])[OH:2])([CH3:15])([CH3:14])[CH3:13]

Participants

6

Reactant 4

HCID 407Phosphonic acidHCID 6385Tert-ButylamineHCID 574694Bis(chloromethyl)phosphinic acid2×HCID 12565361HCID 12565361, compound

Product 1

HCID 88799872HCID 88799872, compoundYield 3.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

It must be presumed that, in the reaction mechanism of this surprising reaction, a four-membered ring intermediate is formed, which is hydrolyzed into the phosphonic acid by water, and that consequently the reaction proceeds in accordance with the following scheme: ##STR6## This reaction mechanism also seems to play a minor part in the reaction of aliphatic primary amines with bis(chloromethyl)phosphinic acid, where it occurs as a troublesome secondary reaction. It has been observed by the applicant for example that, in the reaction of bis (chloromethyl)-phosphinic acid with tert-butylamine in accordance with M. K. Il'ina and I. M. Shermergorn, Bull. Acad. Sci. USSR, 1968, page 1759 (English edition), not only is the desired bis(tert-butylaminomethyl)phosphinic acid described in this reference obtained in 30.4% yield, but also small amounts (3.2%) of tert-butyl-methylaminomethylphosphonic acid of the formula ##STR7## simultaneously result. Likewise, in the reaction of bis(chloromethyl)phosphinic acid with methylamine, a small amount of dimethylaminomethylphosphonic acid

Workup

  1. customin the reaction mechanism of this surprising reaction
  2. customa four-membered ring intermediate is formed
  3. customoccurs as a troublesome secondary reaction

Sources & evidence

ORD record
ord-08494c33303d40ce97b7f92740c65ebf
Source dataset
uspto-grants-1979_07
Patent number
US04160779

Reaction notes

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