Acetanilide, «-benzoyl

Acetanilides, benzoyl-colour couplers in colour photography, 1, 372 Acetanilides, pivaloyl-colour couplers in colour photography, 1, 372 Acetazolamide — see l,3,4-Thiadiazole-2-sulfonamide, 5-acetamido-Acetic acid, acetamidocyano-ethyl ester, 1, 307 Acetic acid, 2-acylphenyl-isochroman-3-one synthesis from, 3, 858 Acetic acid, 3-benzo[6]thiophenyl-biological activity, 4, 912 Acetic acid, l,2-benzoxazol-3-yl-electrophilic substitution, 6, 48... 

Abietic ACID, 32, 1 acid sodium salt of, 32, 4 diamylamine salt of, 32, 2 Acetaldehyde, 36, 60 Acetaldehyde, diphenyl-, 38, 26 Acetal formation, from pentaerythritol and benzaldehyde, 38, 65 Acetamide, 31, 17 Acetamide, N-bromo, 31,17 a-PHENYL-, 32, 92 Acetanilide, < -benzoyl-, 37, 2 Acetanilide, -benzoyl-2-methoxy-4-nitro, 37, 4... 

Yellow Couplers. The most important classes of yeHow dye-forming couplers are derived from P-ketocarboxamides, speciftcaHy the benzoyl acetanilides (6) (66) and the pi val oyl a ceta n il i des (7) (67). Substituents Y and Z can be used to attach baHasting or solubilization groups as weH as to alter the reactivity of the coupler and the hue of the resulting dyes. Typical coupling-off groups (X) cited in the Hterature are also shown. 

The relatively low pX values seen for the benzoyl acetanilides, especiaHy as two-equivalent couplers, minimize concerns over slow ionization rates and contribute to the couplers overaH reactivity. But this same property often results in slow reprotonation in the acidic bleach, where developer carried over from the previous step can be oxidized and react with the stiH ionized coupler to produce unwanted dye in a nonimage related fashion. This problem can be eliminated by an acidic stop bath between the developer and the bleach steps or minimized by careful choice of coupling-off group, coupler solvent, or dispersion additives. 

The lack of a second aryl group flanking the active methylene site, however, means that the pX values of the pi val oyl a ceta n il i des tend to be considerably higher than those of the benzoyl acetanilides. As a result, these couplers are rarely used as thek four-equivalent parents. Rather, the coupling... 

Can it promote vinyl polymerization initiated with Ce(IV) ion Dong et al. [37-39] for the first time reported that AAA and its derivatives such as o-acetoacetotolu-idine (AAT), o-acetoacetanisidide (AAN), and 2-benzoyl acetanilide (BAA) possess very high reactivity toward Ce(IV) ion in initiating the polymerization of vinyl monomer. The results are tabulated in Table 3. 

Friedel-Crafts alkylations and acylations of N-arylamides also proceed normally. For example, benzoylation of acetanilide (iV-acetylaniline) under Friedel-Crafts conditions gives 4-aminobenzophenone in 80% yield after hydrolysis. 

Substituted amides suffer hydrolysis with greater difficulty. The choice of an acid or an alkaline medium vill depend upon (a) the solubility of the compound in the medium and (b) the effect of the reagent upon the products of hydrolysis. Substituted amides of comparatively low molecular weight (e.g., acetanilide) may be hydrolysed by boiling either with 10 per cent, sodium hydroxide solution or with 10 per cent, sulphuric acid for 2-3 hours. Other substituted amides are so insoluble in water that little reaction occurs when they are refluxed with dilute acid or dilute alkali for several hours. These include such substances as benzanilide (C(H(CONHC,Hg) and the benzoyl derivative of a naphthylamine (C.HjCONHCioH,) or a toluidine (C gCONHCjH,). For these substances satisfactory results may be obtained with 70 per cent, sulphuric acid this hydrolysis medium is a much better solvent for the substituted amide than is water or more dilute acid it also permits a higher reaction temperature (compare Section IV 192) ... 

Primary and secondary amines are acylated by acid chlorides and anhydrides, in particular also by the chloride of benzene sulphonic add (p. 192). The preparation of acetanilide has already been described (pp. 125, 128). The acetyl- and benzoyl-derivatives of all the simpler primary amines of the benzene and naphthalene series are known, so that these derivatives can always serve for purposes of identification. 

Yellow Couplers and Dyes. All the useful yellow couplers are based on acetanilides, especially the pivaloyl and benzoyl derivatives (2.83), which react to give the azomethine dyes (2.84) absorbing at wavelengths in the region 450 80 nm. 

This reaction has been applied to a great number of carbonyl compounds, e.g., cyclopentanone,27 1,3-cyclohexanedione,36 5,5-dimethyl-l,3-cyclohexanedione,S5 1-acenaphthenone,24,25 1,3-indane-dione,35 1,3-phenalanedione,85 86 sodium salts of 3-aryl-3-oxo-propanals,39 2,3-dihydrobenzo[6]thiophen-3-one,40 sodium benzoyl-acetate,41 benzoylacetonitrile,29 30,88 ethyl cyanoacetate,30 35 cyano-acetanilide,30 barbituric acid,35 rhodanine,35 jV-phenylrhodanine,37 and iV-methylenebenzothiazoline.37... 

Idemify and account for the producl(s) expected from each of the following reactions (a) benzene + benzoyl chloride + AlCI (b) acetanilide + nitric acid + sulfuric acid (c) bromobeiizene + sulfuric acid (d) l-melhoxy-2-nitrobenzene + nitric acid + sulfuric acid (e) (trif1 uoromethyI)benzene + Bi + Fe powder. 

Ethyl benzoylacetate, CgHjCOCHjCOjCjH, reacts with concentrated ammonium hydroxide in the cold or with aniline in xylene at 150° to give the corresponding -keto amides, benzoylacetamide (81%) and benzoyl-acetanilide (76%), respectively. 

Iodine in trace amounts has been used as catalyst in Friedel-Crafts acylations of furane and thiophene and of more active members of the benzene series such as anisole and acetanilide. " Oddly enough, it is not effective for benzoylation of anthracene.""... 

Properties White to reddish crystals and powder. Related to acetanilide, containing benzoyl in place of acetyl radical. D 1.306, mp 160-162C. Soluble in alcohol insoluble in water slightly soluble in ether. 

A very efficient cyclization of o-acyl-cu-substituted acetanilides is effected by heating them with a base the cu-substituent should be electron-withdrawing. Suitably positioned acetyl and benzoyl functions undergo an aldol condensation alumina as a base gave better results than potassium carbonate. 

Methylaminocarbonyloxy)- 996 2-(N-Methyl-anilinocarbonyl-methoxy)-aus 2-Ethansulfonyl-1,3-benzothiazol und Hydroxy-essigsaure-(N-ntethyl-anilid) 980 aus Kaliumhydroxid/2-Hydroxy-N-methyl-acetanilid/2-Chlor-l, 3-benzothiazol 970 2-(N-Methyl-anilino)-4,5,6,7-tetrahydro- 14 2-(4-Methyl-benzoyl)- 954... 

Although most of the literature describes benzoylation with zeolites, most acidic solids are effective in benzoylation with benzoyl chlorides. For example, hydrated zirconia [32] has been used for the benzoylation of naphthalene (Eq. 14) and acetanilide (Eq. 15), with yields > 80%. 

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