Acetanilide a-

Fig. 2. Plots of reciprocal energy transfer efficiency (y) against the concentration of benzene (B) and against reciprocal concentration of acetanilide (A) by the photo-rearrangement of acetanilide in cyclohexane, (o) 2-Aminoacetophenone ( ) 4-amino-acetophenone.

Friedel-Crafts allq lations and acylations ofA -aiylamides also proceed normally. For example, benzoylation of acetanilide (A/-acetylaniline) under Friedel-Crafts conditions gives 4-aminobenzophenone in 80 yield after hydrolysis ... 

A -Methyl acetamide was the only product observed in the reaction of acetone oxime at 325° at higher temperatures, acetamide decomposition was observed. Acetophenone oxime yielded acetanilide (A) and. V-methylbenzamide (B). The high ratio of A to B is in accord with the... 

Chloro-N-isopropyl acetanilide a-Chloro-N-isopropylacetanilide. See Propachlor... 

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... 

Bromine is a good electrophile, and acetanilide a good nucleophile, due to the presence of the donating amide nitrogen. Electrophilic aromatic substitution (SfAr) by the bromine gives the aryl bromide product, in which substitution of Br" occurs at the o-position. 

The basicity of amines and the solubility in water of amine salts can be used to separate water-insoluble amines from water-insoluble, nonbasic compounds. Shown in Figure 23.2 is a flowchart for the separation of aniline from acetanilide, a neutral compound. 

One of the most important examples is the chlorosulfonation of acetanilide 13 to /7-acetamidobenzenesulfonyl chloride 14 (Equation 38), since the latter is used as an intermediate in the manufacture of sulfonamide antibacterial drugs. The optimum reaction conditions were found to be the use of a relatively large excess of the reagent (five equivalents) at 60 °C (2 hours). In acetanilide (A -phenylacetamide) 13, the bulky acetamido (MeCONH) group is electron-donating (+M effect) and its large size virtually excludes o-sulfonation, so the / -sulfonyl chloride 14 is isolated as almost the sole product. 

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