Phenyl- -anilid

Diphenylmethyl-phenyl- -anilid El, 236 Diphenyl- -methylsulfonyloxyamid El, 597 Diphenyl- -raorpholid E2, 237 Diphenyl- -(4-nitro-benzoylamid) E2, 240 (l,5-Diphenyl-3-oxo-4-penten-yl)-phenyl- XII/1,... 

Derivate 333 Phenyl- -anilid 333 Phenyl- -(N-benzoyl-anilid) 333... 

Amino-benzoesaure-N-(4-amino-phenyl)-anilid (R1 = 4-NO,—C6H4 R2 = 4-NH,-C6H4) 65% d.Th. ... 

Anilides and a-Naphthalides. The Grignard reagents prepared from alkyl halides react with phenyl isocyanate (CgHjN=C=0) or with a-uaphthy l isocyanate (C,oH, N=C=0) to yield addition products that are converted by hydrolysis into anihdes and a-naphthalides respectively RX + Mg —> RMgX... 

Acid B.P. M.P. 1 Anilide /hToIuI- dlde Amide phcnacyl Ester Nltro- benzyl Ester /)-Phenyl- phenacyl Ester S-Benzyl> Mo-thlu- ronlum Salt -Bromo- anlUde Hydrazlde ... 

Salicyl-u-toluide has been prepared only by the action of phosphorus oxychloride upon a mixture of salicylic acid and o-toluidine. The useful methods of preparation of salicylanilide are by the interaction of salicylic acid and aniline in the presence of phosphorus trichloride, by heating phenyl salicylate and aniline, and from o-hydroxybenzamide and bromobenzene in the presence of small amounts of sodium acetate and metallic copper. A number of these and other anilides have been described. ... 

Toliiic anilide, on hydrolysis, forms toluic acid and aniline, whereas beii2oic toluide yields benzoic acid and toluidine. It follows therefoie that, in the original compound, the first contains the hydroxyl neaier the phenyl group and the second nearer the tolyl group. 

Enamines of cyclic ketones do not form cycloaddition products, but give the mono- or dicarboxanilides (110,111). Thus the enamine (113) on reaction with 1 equivalent of phenyl isocyanate gave 160. Treatment of 113 with 2 equivalents, or 160 with 1 equivalent, of phenyl isocyanate gave the 2,6-disubstituted product (161). Mild acid hydrolysis of 160 and 161 produced the corresponding cyclohexanone(2-mono- and 2,5-di)carbox-anilides (110). 

It yields the following crystalline derivatives, which are suitable for its identification nitrosochloride melting at 103°, nitrol-piperidine melting at 108°, nitrol-anilide melting at 110°, and phenyl-urethane melting at 85°. 

Originally, 2-diazophenols were used as diazo components. Nowadays the most important compound is 2,5-diethoxy-4-morpholinobenzenediazonium tetrafluoro-borate. Typical coupling components are acetoacetic anilide, l-phenyl-3-carbamido-... 

Auf diese Weise erhalt man aus N-Phenyl-phthalimid 2-Hydroxymethyl-benzoesaure-anilid (92% d.Th. F 1440)2. Beider Reduktion von Phthalimid in waBrigem Isopropanol wird Phthalid gebildet5 ... 

Lithium anilide reacts with phenyl- or methyltin trichloride to give polynuclear Sn-N compounds, in which the phenyltin derivatives are four-coordinate and bicyclic (Equation (168)), and the methyltin derivatives are five-coordinate and tetracyclic.504... 

The aromatic amides have attracted considerable interest from the photochemical point of view. However, anilides are less prone to photochemical rearrangements than the analogous phenyl esters. For this reason, the side reactions involving other parts of the molecule may compete favorably with PFR. Shizuka started the study of anilides in the 1960, and thereafter a number of papers have appeared dealing with the PFR of A -acyl anilines, carbazoles, indoles, and so forth. 

A multigram preparation of a useful chiral building block was developed, using the Beckmann rearrangement as a key synthetic step (equation 115) °. The enantiomeric addition of thiophenol to a chalcone 313, catalysed by (+)-cinchonine, provided the chiral enantiomeric carbonyl compound 314. The Beckmann rearrangement of its oxime 315 gives the anilide of (R)-(- -)-3-phenyl-3-phenylsulfanylpropanoic acid 316. Alcoholysis produced the expected enantiomerically pure ethyl ester 317. 

Electric dipole moment studies have provided excellent support for the formulation of certain heterocycles as mesoionic compounds. Hanley et al. <78JCS(P1)600> have measured dipole moments for mesoionic l,2,3,4-thiatriazol-5-imines (20), 5-ones (21) and 5-ylidenemalononitriles (22) using a vector analysis similar to that previously employed for sydnones and other mesoionic compounds assuming that mesoionic rings are regular pentagons. The dipole moment of 3-phenyl-1,2,3,4-thiatriazolium-5-anilide (20) was found to be 3.71 D and five derivatives of compounds (21) were measured and the ring moment calculated to be 3.8 D. In both cases the dipole moments are rather small but clearly consistent with the mesoionic formulation. 3-Phenyl-l,2,3,4-thiatriazolium-5-dicyanomethanide (22) was found to have a dipole moment of 8.84 D. 

Dialkylquinazolines 825 are available by microwave-assisted amination and ring closure of 2-acylamino phenyl-ketones 824 with ammonium formate <20070L69>. The 2-aminophenyl ketone precursors of the amides 824 are available by a photochemically induced Fries rearrangement of anilides 823, which enables a variety of different alkyl substituents to be incorporated at the 4-position of the quinazoline <20070L69>. 

For amides obtained by stereospecific ring opening of (Z)- and ( )-2-phenyl-4-(a-phenylethylidene)-5(477)-oxazolone 505 and 508, cyclization gives the imida-zolone 510 or 4-methyl-l-phenyl-3-isoquinolinecarboxylic acid anilide 507. The products are determined by the double-bond geometry in the starting material and by the experimental conditions (Scheme 7.161). ... 

Die durch Fluorid-Ionen induzierte Cyclisierung von Dichlor-essigsaure-[N-(2-trimethylsilyl-oximino-propyl)-anilid] fiihrt direkt zu 2-Formyl-4-methyl-l-phenyl-imidazol-3-oxidni. Die eigentlich erwartete 2-Dichlormethyl-Verbindung konnte nicht isoliert werden. 

Kohlensaure-anilid-(2-benzoyl-hydrazid) reagiert mil Dichlor-triphenyl-phosphoran/Triethyl-amin iiber Benzonitril-(anilinocarbonyl-imin) in einer 1,5-Elektrocyclisierung zu 2-Anilino-5-phenyl-1,3,4-oxadiazol (87% Schmp. 21 4 2 1 5 )420 ... 

Bei der Umsetzung von 3,4-Dibenzoyl-furazan-2-oxid mit Anilin isoliert man zunachst das instabile 2-Hydroximino-3-oxo-3-phenyl-propansaure-anilid-hydroximid (IV)420 421, aus dem liber 3-Anilino-4-nitroso-5-phenyl-l, 2-oxazol (III)422 4-Anilino-3-benzoyl-furazan (V 80%) ent-... 

Neither the anilide of cinnamic acid94 nor the diphenyl substituted acroyl anilide 138 95 yields any product of rearrangement or cyclodimerization. Upon irradiation of 138 in benzene solution in a Pyrex reactor, only the isomeric /9-lactams 139 (2.3%) and 140 (37%), in addition to dihydrocarbostyril 141 (5%), were isolated. The latter is the major product upon irradiation of alkyl substituted acroyl anilides.96 On the other hand, the closely related phenyl cinnamate rearranges regularly to the ortho- and para-positions97 and does not dimerize as the other alkyl esters of cinnamic acid.98... 

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