Sciencemadness Discussion Board
Not logged in [Login ]
Go To Bottom

Printable Version  
Author: Subject: Reaction of esters with hydrazine?
National Hazard

Posts: 962
Registered: 19-5-2002
Location: American Midwest
Member Is Offline

Mood: pyrophoric

[*] posted on 7-9-2002 at 15:31
Reaction of esters with hydrazine?

I know for a fact that esters of carboxylic acids will react with ammonia to form an amide and an alcohol. I'm wondering if there would be a similar reaction with hydrazine - my first guess would be that there isn't. But still, the idea interests me. Can anyone enlighten me?

Perhaps something like this would happen?

(COOCH3)2 + N2H4 ----> (CONH)2 + 2CH3OH

I weep at the sight of flaming acetic anhydride.
View user's profile View All Posts By User
on fire

Posts: 122
Registered: 7-8-2002
Member Is Offline

Mood: No Mood

[*] posted on 8-9-2002 at 04:44
Not Likely In That Way

I bet hydrazine would react with esters, but I think it highly unlikely for it to easily form a cyclic compound like you have pictured there.

I think that one hydrazine moietywill react with one moiety of ester, and if enough hydrazine is present for further reaction, another moiety of hydrazine might then react with the other moiety of ester in that compound, giving the diamide-like structure.

I seriously doubt that cyclization would so readily occur because for it to do so, the hydrazine-amide of one ester would have to ionically react with the other ester, and the hydrazine amide is unlikely to bear a negative charge needed to do so through common mechanisms. Even if it did work, other free hydrazine molecules would have far better odds of reacting with the remaining ester function first, and so the yields of truly cyclic diamides would be minimal.

There may of course be some reaction conditions that do promote that reaction. Anything is possible, I am just saying that the reaction of putting the two together is not likely to produce that compound without some sort of "external influence of will" of some sort, on the chemist's behalf. ;)

View user's profile View All Posts By User
PHILOU Zrealone
International Hazard

Posts: 2893
Registered: 20-5-2002
Location: Brussel
Member Is Offline

Mood: Bis-diazo-dinitro-hydroquinonic

smile.gif posted on 10-4-2003 at 15:18

1)CH3-O2C-CO2-CH3 + H2N-NH2 --> NH2-NH-CO-CO2-CH3 + CH3OH
2)NH2-NH-CO-CO2-CH3 + H2N-NH2 --> (NH2-NH-CO)2 + CH3OH
3)NH2-NH-CO-CO2-CH3 + CH3-O2C-CO2-CH3 --> CH3-O2C-CO-NH-NH-CO-CO2-CH3 + CH3OH

1) equimolar
2) exces NH2-NH2
3) excess ester

CH3-O2C-CH2-CO2-CH3 + H2N-NH2 -heat-> CH3-O2C-CH2-CO-NH-NH2 + CH3OH -heat-> cyclo(-NH-CO-CH2-CO-NH-) + CH3OH


PH Z (PHILOU Zrealone)

"Physic is all what never works; Chemistry is all what stinks and explodes!"-"Life that deadly disease, sexually transmitted."(W.Allen)
View user's profile View All Posts By User

  Go To Top