Tris(2-chloroethyl) phosphite → {[Methyl(methylcarbamoyl)amino]methyl}phosphonic acid

HRID 1576290Notes

Reaction equation

HRID 1576290 reaction equation
[P:1]([O:10]CCCl)([O:6]CCCl)[O:2]CCCl.[CH3:14][N:15]1[C:19](=[O:20])[N:18]([CH3:21])[CH2:17]P1(=O)OCCCl>C(O)(=O)C.O>[CH3:17][N:18]([CH2:21][P:1](=[O:2])([OH:6])[OH:10])[C:19]([NH:15][CH3:14])=[O:20]

Participants

4

Reactant 2

HCID 8783Tris(2-chloroethyl) phosphiteHCID 21501243HCID 21501243, compound

Product 1

HCID 21718273{[Methyl(methylcarbamoyl)amino]methyl}phosphonic acid

Reagents, catalysts & solvents 1

HCID 21899381Acetic acid--water (1/1)Solvent

Procedure

This phosphonic acid is prepared in a similar manner using tris(2-chloroethyl) phosphite as the phosphorus ester reactant. The crude intermediate 1,4-dimethyl-2-(2-chloroethoxy)-1,4,2-diazaphospholidin-5-one-2-oxide (31P nmr -24.9 ppm) is hydrolyzed without isolation from the reaction mixture to give the acid: mp 171°-172° dec. (acetic acid-water).

Workup

  1. customto give the acid

Sources & evidence

ORD record
ord-7b6cf517aed540d995728e0e8fb0bbcb
Source dataset
uspto-grants-1976_09
Patent number
US03980618

Reaction notes

Loading…