Hockeydemon
Hazard to Others
Posts: 218
Registered: 25-2-2013
Member Is Offline
Mood: No Mood
|
|
Carbolithiation of N-alkenyl ureas to a hindered amine?
This is probably outside of my capabilities, but I figured I'd ask about the possibility of it.
I was thinking I could perform a SN2 reaction with
1-butanol + HCl --> chlorobutane
Then react chlorobutane with lithium to form the super base n-Butyllithium
Then synthesize a alkenylcarboxlate (haven't decided on a route)
Then react the alkenylcarboxlate with urea to form n-alkenyl urea
Then a carbolithiation of N-alkenyl urea with the n-butyllithium which results in a hindered amine.
I'm not really sure what I would use a hindered amine for, but I stumbled across these while looking for various reactions to perform.
[Edited on 30-7-2013 by Hockeydemon]
|
|
|
bbartlog
International Hazard
Posts: 1139
Registered: 27-8-2009
Location: Unmoored in time
Member Is Offline
Mood: No Mood
|
|
See whether you can do the first step. Seems to me like it would be dog slow without ZnCl<sub>2</sub> catalysis. Or you could use HBr and
end up with 1-bromobutane instead - that prep is described in 'Experiments in Organic Chemistry', in the forum library. No catalyst needed for that
one.
The less you bet, the more you lose when you win.
|
|
|
Hockeydemon
Hazard to Others
Posts: 218
Registered: 25-2-2013
Member Is Offline
Mood: No Mood
|
|
Quote: Originally posted by bbartlog  |
See whether you can do the first step. Seems to me like it would be dog slow without ZnCl<sub>2</sub> catalysis. Or you could use HBr and
end up with 1-bromobutane instead - that prep is described in 'Experiments in Organic Chemistry', in the forum library. No catalyst needed for that
one.
|
I went ahead and added 2mL HCl & 2mL 1-butanol to 3mL H2O with a dash of NaCl. I then proceeded to heat that with a bunsen burner. There are now
two immiscible layers in the test tube, the top layer is a incredibly light tan/slightly cloudy (would be clear without the contrasting lower layer)
while the bottom layer is slightly cloudy, but more clear than the top layer.
I'm not sure how to test to see if I made chlorobutane, but I'll start googling I guess.
|
|
|
bbartlog
International Hazard
Posts: 1139
Registered: 27-8-2009
Location: Unmoored in time
Member Is Offline
Mood: No Mood
|
|
Sounds like you salted out your butanol from the aqueous, briny part of your HCl. The layers are not evidence for a reaction, in other words.
I don't know of a qualitative test for chlorobutanol but if I were to attempt this I would want reflux gear, and large enough reagent volumes that I
could take a boiling point on the vapors as they distilled over.
The less you bet, the more you lose when you win.
|
|
|
![[*]](images/xpblue/default_icon.gif){kind=icon}
