A-Chloro-2,6-dimethylacetanilide

Lidocaine Lidocaine, 2-(diethylamino)-A-(2,6-dimethylphenyl)acetamide (2.2.2), is synthesized from 2,6-dimethylaniline upon reaction with chloroacetic acid chloride, which gives a-chloro-2,6-dimethylacetanilide (2.1.1), and its subsequent reaction with diethy-lamine [11]. 

Setting Up Oven-dry the glass apparatus for heating under reflux. Dissolve 2.2 g of dry a-chloro-2,6-dimethylacetanilide in 30 mL of toluene in the dry round-bottom flask containing a stirbar. Assemble the apparatus for heating under reflux. 

Reaction Add 2.4 g of diethylamine to the solution of a-chloro-2,6-dimethylacetanilide with stirring, and then heat the reaction mixture under reflux for 90 min. Allow the mixture to cool to room temperature, and then cool it briefly in an ice-water bath. 

Consider the spectral data for a-chloro-2,6-dimethylacetanilide (Figs. 21.26 and 21.27). 

Discuss the differences observed in the IR and NMR spectra of 2,6-dimethylaniline and a-chloro-2,6-dimethylacetanilide that are consistent with the formation of the latter in this procedure. 

So far only certain details of the biochemical mode of action of metolachlor are known. Pillai and Davis (1975) found that in 2 hours metolachlor at a concentration of 110 mole/dm reduced the photosynthesis of Chlorella pyrenoidosa by 33%. It is remarkable that the other structural analogue investigated CGA 17020, 2-chloro-N-(2-methoxyethyl)-2,6-dimethylacetanilide, does not inhibit photosynthesis at this concentration. 

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