Sodium chloroacetate synthesis

Yield:-

Reaction Conditions:

with sodium carbonate in water at 45;

Steps:

A3.1
A3. i-Acetyl-θ-chloro-IH-indol-S-yl acetateStep 1 : 2-[(Carboxymethyl)amino]-4-chlorobenzoic acid. Chloroacetic acid (15 g) is dissolved in water (15 ml) and sodium carbonate (16 g) is added in portions (carbon dioxide evolves) and the mixture is stirred at 45⁰C for 30 min. In parallel, 2-amino-4-chlorobenzoic acid is dissolved in water (15 ml), 1 M aqueous sodium hydroxide solution (15 ml) is added, followed by the sodium chloroacetate solution prepared above. The resulting mixture is stirred at 6O⁰C for 2 days. After cooling, 1 M aqueous sodium hydroxide solution is added, after that, it is acidified by addition of concentrated hydrochloric acid. The yellow precipitate, that is formed, is filtered off and washed with water (100 ml). It is redissolved in tetrahydrofuran / ethyl acetate (1 :1 (v/v), 150 ml), dried (Na₂SO₄) and concentrated in vacuo. The residue, 20.0 g of crude 2-[(carboxymethyl)amino]-4-chlorobenzoic acid as a yellow solid, is used without further purification in the next step.

References:

NYCOMED GMBH;BARTELS, Björn;WEINBRENNER, Steffen;MARX, Degenhard;DIEFENBACH, Jörg;DUNKERN, Torsten;MENGE, Wiro M.P.B.;CHRISTIAANS, Johannes A. M. WO2010/15589, 2010, A1 Location in patent:Page/Page column 107

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