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Topic: Does the PCl3 reaction with 4-aminobutyric acid insitu to form acyl chloride  (Read 5608 times)

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bharathi

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hi all,
I have been struggling to find out the mechanism by which the following reaction occurs. Plz guide me.

Phosphorus trichloride (3 moles) is added to a mixture of phosphorus acid (H3PO3, 1mole), 4-amino butyric acid in   p-cresol as solvent medium at ambient temperature and then heated to 60 deg C & maintained for several hours.
Water is then charged and temperature raised to 100 deg C and maintained till reaction completion.
Organic layer is then separated & discarded.
The product formed is 4-amino-1-hydroxybutylidene-1,1-bisphosphonic acid

Does the PCl3 reaction with 4-aminobutyric acid insitu to form acyl chloride and then react with phosphorus acid??
What is the role of phosphorus acid??
Is this a named organic reaction??

I guess that water addition aids in hydrolysis of phosphorus acid to phosphoric acid and HCl, the phosphoric acid reacts with p-cresol to form tricresyl phosphate which is the discarded organic layer.
Is this correct??

Plz guide me in arriving at the probable mechanism for the formation of the product.

Regards,
Bharathi
« Last Edit: October 27, 2005, 01:45:27 AM by Mitch »

Offline movies

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Re:mechanism
« Reply #1 on: October 25, 2005, 12:01:10 PM »
I think that you have the right idea with the formation of the acid chloride.  I bet this reaction does have a name, but I don't know what it is.

laotree

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"A nonhormonal medication for the treatment of postmenopausal osteoporosis in women. This drug builds healthy bone, restoring some of the bone loss as a result of osteoporosis." Are you making this drug?


Offline bartnik

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Re: 4-amino-1-hydroxybutylidene-1,1-bisphosphonic acid
« Reply #3 on: March 13, 2008, 02:00:29 PM »
For melting point of 4-amino-1-hydroxybutylidene-1,1-bisphosphonic acid see:
 http://www.aminophosphonic.eu/

Offline Arkcon

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Whoo-hoo.  If they'd actually asked for it, I think they would have found it themselves 2 and a half years ago.
Hey, I'm not judging.  I just like to shoot straight.  I'm a man of science.

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