[Jd1828]

Im looking for a literature source that gives the conditions for such a reaction.  Does anyone know of one?

[HP]

R-NH2 + ClCH2COO:- --> R-NHCH2 COO:-
Basic conditions(NaOH or NaHCO3) heat about 60- 80C...

[Jd1828]

I was actually thinking more like this

R-NH2 + ClCH2COO:- --> R-N-CH2COOH

[HP]

In basic conditions COOH exist as salt eg COO:-Na+ so and the product will be R-NHCH2COONa If you wont to obtain the acid product you should acidify with HCl for example

[Jd1828]

Thanks!  I have a source that shows a secondary amine reacted with chloroacetic acid with similar conditions that you gave.  I just wasnt sure if it would work the same for a primary amine.

[Jd1828]

Im still looking for a source for this reactions.  Im having a hard time finding one for some reason.  

[akitch4]

Did you ever end up having any luck with this? I am in a similar situation now.

[wildfyr]

Have you tried scifinder or Reaxys? I personally feel that bicarb and heat in a polar aprotic solvent would probably do the trick. using wet solvent might be necessary to ensure you don't make any amide.

[criss]

I've done the following reaction:
Ar-NH2 with chloracetic acid in the following way:

  3 g of acid was neutralized with 11-12 mL of NaOH 2N, aniline was added in portions (3 times) in about 2 or 3 minutes (3 mL) and reflux up to completion of the amine (in my case yellow layer of aniline), otherwise monitoring by TLC. (about 2 hours in my case). cooling (usually crystallization) and checking the pH (if it is basic correction with diluted acid) up to 7.
  in my case works as charmed
good luck

[Babcock_Hall]

How does one avoid overalkylation of the amine (meaning reaction of the secondary amine product with a fresh molecule of chloroacetic acid?

[Doc Oc]

The tendency for overalkylation is overstated in undergraduate courses. I've done lots of alkylations of primary amines in refluxing DMF and the majority of product tends to be single alkylation. Only with really reactive electrophiles do you have a problem.