Chloroacetanilides

Phenyl o-radicals generated by reduction of aryl halides can also interact with an intramolecular alkene bond. Ihe method has been developed for the formation of dihydroindoles by reductive cyclization of N-allyl-2-chloroacetanilides. The results indicate the importance of a time interval between electron addition to give a radical-anion and the fragmentation of this species to give the active a-radical, The time interval allows the radical-anion to diffuse away from the electrode surface so that when the a-radical is foimed, it has time to cyclize before it can be reduced at the surface. 

The 2-chloroacetanilides (Figure 2.22) are also suggested to inhibit cell division in susceptible weeds. These compounds have found a major commercial market for the pre-emergence control of grass and some small seeded broad-leaved weeds in crops such as maize and soybean. It is likely that 2-chloroacetanilides also alkylate the sulfhydryl groups of certain essential plant enzymes. 

N-(Butoxymethyl)-2-chloro-N-(2,6-diethylphenyl)aoetamide. Acetamide, N-(butoxymethyl)-2-chloro-N-(2,6-diethyl-phenyl)- Acetanilide, 2-ch oro-2, 6 -diethyl-N-(butoxy-methyl)- Acetanilide, N-(butoxymethyl)-2-chloro-2, 6 -diethyl- Amichlor Bilchlor BRN 2873811 Butachlor Butaclor Butanex Caswell No, 119B 2-Chloro-2, 6 -diethyl-N-(butoxymethyl)acetanilide CP 53619 Del-ohlor Delchior 5G 2, 6 -Diethyl-N-butoxymethyl-2-chloroacetanilide 2,6 -Diethyl-N-butoxymethyl-a-chloro-acetanilide EINECS 245-477-8 EPA Pesticide Chemical Code 112301 Hiltachlor HSDB 6865 Mach-Mach Machete Machete (herbicide) Machetfe N-(Butoxymethyl)-2-chloro-N-(2,6-diethylphenyl)acetamide N-... 

Ammo-5,6,7,8-tetrabromo-4-tolyl-l(2/i/)-phthalazinone (72) underwent sub-stituted-alkylation by 2-chloroacetanilide to give 5,6,7,8-tetrabromo-2-[(iV-phenylcarbamoylmethyl)aniino]-4-tolyl-1 (2f/)-phthalazinone (72a) (reactants, EtOH, reflux, 4h 73% o, m, or -tolyl unspecified). ... 

N-lsopropyl-2-chloroacetanilide N-lsopropyl-a-chloroacetanilide. See Propachlor lsopropyl-3-chlorocarbanilate. See Chlorpropham... 

Synonyms 2-Chloro-N-isopropyl acetanilide a-Chloro-N-isopropylacetanilide 2-Chloro-N-isopropyl-N-phenylacetamide 2-Chloro-N-(1-methylethyl)-N-phenylacetamide N-lsopropyl-2-chloroacetanilide N-lsopropyl-a-chloroacetanilide Empirical CnHuCINO... 

Synonyms Albrass Bexton Bexton 4L 2-Chloro-A-isopropylacetanilide a-Chloro-7V-isopropylacetanilide 2-Chloro-A-(l-methylethyl)-A-phenylacetamide CP 31393 N-Isopropyl-2-chloroacetanilide A-Isopropyl-a-chloroacetanilide Niticid Propachlore Prolex Ramrod Ramrod 65 Satecid. 

Bromoacetanilide is slightly less reactive toward further electrophilic substitution than acetanilide, but it is still sufficiently reactive to be chlorinated under mild conditions without a strong Lewis acid catalyst. Thus, molecular chlorine dissolved in acetic acid chlorinates 4-bromoacetanilide to produce 4-bromo-2-chloroacetanilide (20) as shown in Equation 21.12. The formation of the 2- rather than the 3-chloro isomer demonstrates the more powerful directing effect of the acetamido group as compared to the bromo substituent. 

Setting Up Mix 11.2 g of crude 4-bromo-2-chloroacetanilide with 20 mL of 95% ethanol and 13 mL of concentrated hydrochloric acid in the flask. Add a stirbar and assemble the apparatus for heating under reflux. 

Would 4-bromoacetanilide or 4-bromo-2-chloroacetanilide be more reactive toward electrophilic substitution Explain. 

Consider the spectral data for 4-bromo-2-chloroacetanilide (Figs. 21.14 and 21.15). 

Discuss the differences observed in the IR and NMR spectra of 4-bromoacetanilide and 4-bromo-2-chloroacetanilide that are consistent with the formation of the latter in this procedure. 

What is the white precipitate that forms during the hydrolysis of 4-bromo-2-chloroacetanilide ... 

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