Acetonitrile → (1-Aminoethylidene)bisphosphonic acid

HRID 1732836Notes

Reaction equation

[P:1]([OH:4])([OH:3])[OH:2].[C:5](#[N:7])[CH3:6]>>[NH2:7][C:5]([P:1]([OH:4])(=[O:2])[OH:3])([P:1]([OH:4])(=[O:3])[OH:2])[CH3:6]

Participants

Reactant 2

HCID 6342Acetonitrile

HCID 107909Phosphorous acid

Product 1

HCID 84770(1-Aminoethylidene)bisphosphonic acidYield 75%

Procedure

Into a reactor like the above were charged 130.5 g phosphorous acid and 69 g Sulfolane-W (tetramethylene sulfone, Shell Chemical Co.). 31.2 g acetonitrile was introduced slowly for 11/2 hours at 140°-150° C. and the reactants were held for additional 81/2 hours at 153°-158° C. The 1-aminoethane-1, 1-diphosphonic acid produced was isolated from the reaction mixture in the manner described in Example 1. The yield was 75% of the theory on the acetonitrile employed.

Workup

custom2 hours
customat 153°-158° C

Sources & evidence

ORD record: ord-2186ac2244ef4fcebb7fdc7d2c40cb6e
Source dataset: uspto-grants-1980_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04239695

Reaction notes

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