2.5- Dimethylacetanilide

De la Mare and Hassan254 obtained second-order rate coefficients (in parenthesis) for the following 4-methylacetanilide (1.53), 2-methylacetanilide (0.193), 2,6-dimethylacetanilide (0.0118), acetanilide (0.93), 4-acetamidodiphenyl (0.248) and 1,4-diacetamidobenzene (0.231) the results for the acetanilides demonstrated the effect of steric hindrance to coplanarity thereby inhibiting resonance of the nitrogen lone pair with the aromatic ring. The rate coefficients for chlorination of 3-chloroacetanilide (0.215), 4-chloroacetanilide (0.010) 3-nitroacetanilide (6.7 x 10 5) and phenyl benzoate (3.2 x 10-6) have also been measured258,261. 

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]. 

Lidocaine Lidocaine is 2-diethylamino-2, 6 -dimethylacetanilide (2.2.3). Synthesis of lidocaine is described in Chapter 2. 

SYNS ANESTACON HYDROCHLORIDE 2-piETHYLAMINO)-2, 6 -ACETOXYLIDIDE MONOHYDROCHLORIDE a-DIETHYLAi IINO-2,5-ACETOXYLIDINE HYDROCHLORIDE 0)-DIETHYLAMINO-2,6-DIMETHYLACETANILIDE HYDROCHLORIDE 2-(DIETHYLAMINO)-N-(2,6-DIMETHYLPHENYL)ACETAi IIDE MONOHYDROCHLORIDE DUNCAINE HYDROCHLORIDE GRAVOCAIN HYDROCHLORIDE ISICAINE HYDROCHLORIDE LEOSTESIN HYDROCHLORIDE... 

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. 

Pd(OAc)2 and an excess of Mel afforded 2,6-dimethylacetanilide (425) by stepwise oft/jo-palladation and methylation twice [179]. However, treatment of the Schiff base complex 426 with trifluoroacetic acid and alkyl iodide produced the 2,6-dialkylbenzaldehyde 427 after hydrolysis. This reaction can be made semi-catalytic [180]. 

Acetic anhydride added to a stirred soln. of 2,6-dimethylaniline in aq. HCl, aq. Na-acetate added as soon as the acetic anhydride has gone into soln., and stirred 1 hr. 2,6-dimethylacetanilide. Y 87%. R. L. Taber et al., J. Heterocyclic Chem. 2, 181 (1965). 

When solutions of potential tt donors are mixed with those having potential tt acceptors, bathochromic shifts in UV/Vis spectra, and upheld shifts in NMR adsorbances serve as physical evidence that complexation has occurred. Figure 28.19 is representation of the UV/Vis spectral change that occurs when tt acceptor V-methy-3,5-dinitrobenzamide (DNB) is complexed with ether bupivacaine hydrochloride or with its model compound 2,6-dimethylacetanilide. 

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. 

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