November 01, 2024, 02:20:10 AM
Forum Rules: Read This Before Posting


Topic: Do esters react with amines ?  (Read 4549 times)

0 Members and 1 Guest are viewing this topic.

Offline shalikadm

  • Full Member
  • ****
  • Posts: 115
  • Mole Snacks: +4/-10
  • Gender: Male
  • smells like isopropyl alcohol
Do esters react with amines ?
« on: June 11, 2012, 10:56:38 AM »
Esters react with concentrate NH3 when heated..Does it happens with amines also ?

Offline discodermolide

  • Chemist
  • Sr. Member
  • *
  • Posts: 5038
  • Mole Snacks: +405/-70
  • Gender: Male
    • My research history
Re: Do esters react with amines ?
« Reply #1 on: June 11, 2012, 10:59:12 AM »
Esters react with concentrate NH3 when heated..Does it happens with amines also ?


Yes.
I have done it by heating in a sealed tube using catalytic KCN. One can also use a Parr apparatus. Yields vary depending on the amine.
Development Chemists do it on Scale, Research Chemists just do it!
My Research History

Offline Babcock_Hall

  • Chemist
  • Sr. Member
  • *
  • Posts: 5688
  • Mole Snacks: +329/-24
Re: Do esters react with amines ?
« Reply #2 on: June 11, 2012, 11:00:42 AM »
Are you interested only in esters derived from methanol, or do you have other alcohols in mind?

Offline shalikadm

  • Full Member
  • ****
  • Posts: 115
  • Mole Snacks: +4/-10
  • Gender: Male
  • smells like isopropyl alcohol
Re: Do esters react with amines ?
« Reply #3 on: June 11, 2012, 11:03:30 AM »
Esters react with concentrate NH3 when heated..Does it happens with amines also ?


Yes.
I have done it by heating in a sealed tube using catalytic KCN. One can also use a Parr apparatus. Yields vary depending on the amine.

Do we have to use a catalytic for that..?
Can't we use a concentrated amine(primary or secondary) and just heat the solution..?

Offline shalikadm

  • Full Member
  • ****
  • Posts: 115
  • Mole Snacks: +4/-10
  • Gender: Male
  • smells like isopropyl alcohol
Re: Do esters react with amines ?
« Reply #4 on: June 11, 2012, 11:06:17 AM »
Are you interested only in esters derived from methanol, or do you have other alcohols in mind?
not only from methanol...any ester..

Offline discodermolide

  • Chemist
  • Sr. Member
  • *
  • Posts: 5038
  • Mole Snacks: +405/-70
  • Gender: Male
    • My research history
Re: Do esters react with amines ?
« Reply #5 on: June 11, 2012, 11:07:34 AM »
Esters react with concentrate NH3 when heated..Does it happens with amines also ?


Yes.
I have done it by heating in a sealed tube using catalytic KCN. One can also use a Parr apparatus. Yields vary depending on the amine.

Do we have to use a catalytic for that..?
Can't we use a concentrated amine(primary or secondary) and just heat the solution..?

Goes better with a catalyst, primary amines are, of course, more reactive than secondary, but if you push it you can get them to react as well.
Development Chemists do it on Scale, Research Chemists just do it!
My Research History

Offline Babcock_Hall

  • Chemist
  • Sr. Member
  • *
  • Posts: 5688
  • Mole Snacks: +329/-24
Re: Do esters react with amines ?
« Reply #6 on: June 11, 2012, 03:46:01 PM »
So called "active esters" form amides with amines.  The first alcohol (to the best of my knowledge) was 4-nitrophenol, and the paper was in JACS in 1959 (Bodzanski might have been the corresponding author, but my memory is uncertain).  Pentafluorophenol is another alcohol that forms active esters.  The pKa of the conjugate acid of the leaving group is lower for an active ester than for a typical ester.

Offline orgopete

  • Chemist
  • Sr. Member
  • *
  • Posts: 2636
  • Mole Snacks: +213/-71
    • Curved Arrow Press
Re: Do esters react with amines ?
« Reply #7 on: June 11, 2012, 06:37:13 PM »
Formate esters and malonate esters are also more reactive to amines.
Author of a multi-tiered example based workbook for learning organic chemistry mechanisms.

Sponsored Links