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

HRID 1729752Notes

Reaction equation

HRID 1729752 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 intermediate ester, 1,4-dimethyl-2-(2-chloroethoxy)-1,4,2-diazaphospholidin-5-one-2-oxide, 31P nmr -24.9 ppm, is hydrolyzed in 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-65547bed59bf4362a230d27fea326402
Source dataset
uspto-grants-1976_11
Patent number
US03989727

Reaction notes

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