All Questions
17
questions
1
vote
0
answers
63
views
Amidine synthesis from nitrile and dimethylamine using n-Buli as a base
I am making LiNMe2 using n-Buli (5.5 equiv.) and dimethylamine (5.0 equiv), -15 ºC, dry THF and under nitrogen atmosphere.
I have been doing the reaction and I can observe conversion of starting ...
- 11
0
votes
0
answers
39
views
Preparation of m-nitroaniline from m-dinitrobenzene [duplicate]
Consulting various Organic Chemistry resources, I have found two reactions for the purpose stated in the subject:
First reaction:
Second reaction:
But, I cannot find the reaction mechanism by which ...
- 607
1
vote
0
answers
58
views
Procedure for laboratory synthesis of tertiary amines [closed]
I am having difficulty finding a procedure for making tertiary amines in the lab, any is fine but I am specifically interested in tributylamine.
- 19
1
vote
1
answer
365
views
Can the guanidinium ion give stable N-nitrosamines under mild metalworking conditions?
Can the guanidinium ion react with inorganic nitrite under mild basic metalworking conditions ($\mathrm{pH\ 8 - 10}$ and temperature $\lt \pu{70^\circ C}$) to give stable N-nitrosamines?
Usually, the ...
- 271
3
votes
1
answer
195
views
Laboratory and commercial preparations of aniline other than reduction of nitroarenes [closed]
Till now I could only find one laboratory preparation of aniline, i.e. reducing nitrobenzene with $\ce{Sn}$ and concentrated $\ce{HCl}$. I'm confused if Hofmann degradation is only commercial.
I'd ...
- 39
5
votes
1
answer
178
views
Synthesis of a weinreb amide from an acid
The following shows the conversion of an acid to a weinreb amide:
It was taken from the IChO 2015 preparatory problem set problem 23. In this two-step synthesis, I am slighly puzzled by the first ...
- 10.7k
6
votes
2
answers
879
views
Reduction of 1,4-benzoquinone in the synthesis of 1,5-diazocane
Synthesize 1,5-diazocane using only benzene as a source of
carbon atoms, and ammonia as the only source of nitrogen atoms.
My attempt: Noticing that the target compound has split the benzene ring, ...
- 1,796
4
votes
1
answer
626
views
Why is ammonium chloride rather than an alkylammonium chloride salt the product of nucleophilic substitution of a chloroalkane by ammonia?
My textbook said that when an excess of ethanolic ammonia is heated with a haloalkane ($\ce{R-X}$) one should give the products as being $\ce{R-NH2}$ and $\ce{NH4Cl}$ as opposed to $\ce{RNH3Cl}$. I ...
- 41
2
votes
1
answer
3k
views
Direct conversion of amides to esters
Rarely does the literature describe the synthesis of esters from amides. I understand that amides are a relatively unreactive functional group but they can easily be hydrolysed to give carboxylic ...
- 21
1
vote
2
answers
303
views
Formation of Lactone from 5-amino-decanoic acid?
As expressed in the title, I am trying to figure out how to form a lactone from 5-amino-decanoic acid. The thing that comes to my mind as a start is the attachment of the amino group ($\ce{NH2}$) to ...
- 153
1
vote
1
answer
3k
views
Do Grignard reagents deprotonate amines?
Can I add Mg/dry ether to 2,4,6-tribromoaniline followed by $\ce{D2O}$ in order to replace the bromines with deuterium?
The reaction I'm proposing is part of a synthetic route as shown below.
4
votes
1
answer
14k
views
What is the mechanism for the reaction of acetyl chloride and aniline?
I want to devise the synthesis of 1,2-dinitrobenzene without producing a large amount of 1,3 or 1,4 products.
In my synthesis I have a step in which I obtain aniline. I would like to know the ...
- 4,197
5
votes
1
answer
1k
views
Attack of amine on amide
I am confused with the last step of clozapine synthesis:
How can the amine group attack the amide group to form the amidine in such acidic environment? Is the intermolecular reaction between an amine ...
- 14.4k
2
votes
2
answers
821
views
Reductive amination of (protected) 3-Oxopropanenitrile: Will azetidin-2-ol be formed via intramolecular ring closure?
What happens during this reductive amination?
I got the first product; the lithium aluminium hydride will reduce the nitrile to an amine. But what about the reductive animation step? As far as I can ...
- 19k
0
votes
2
answers
2k
views
Sodium cyanoborohydride and iminium reductions
I understand that the LAH will reduce the nitrile into a primary amine. The addition of acid will likely destroy the acetal mask and leave us with ethylene glycol and a molecule with both a ketone and ...
- 19k