P-Toluidides

Amides, anilides and p toluidides. The dry acid is first converted by excess of thionyl chloride into the acid chloride ... 

The by-products are both gaseous and the excess of thiouyl chloride (b.p. 78°) may be readily removed by distillation. Interaction of the acid chloride with ammonia solution, aniline or p-toluidiiie yields the amide, anilide or p-toluidide respectively ... 

Anilides and p-toluidides may also be prepared directly from the acide% by heating them with aniline or p toluidine respectively ... 

The above simple experiments illustrate the more important properties of aliphatic acid chlorides. For characterisation, the general procedure is to hydrolyse the acid chloride by warming with dilute alkali solution, neutralise the resulting solution with dilute hydrochloric acid (phenol-phthalein), and evaporate to dryness on a water bath. The mixture of the sodium salt of the acid and sodium chloride thus obtained may be employed for the preparation of solid esters as detailed under Aliphatic Acids, Section 111,85. The anilide or p-toluidide may be prepared directly from the acid chloride (see (iii) above and Section III,85,i). 

Anilides or p-toluidides of acids from esters. Esters are converted into the corresponding anilides or p-toluidides by treatment with anilino- or with p-toluidino-magnesium bromide, which are readily obtained from any simple Grignard reagent and aniline or p-toluidine ... 

Acyl hahdes may be identified by —hydrolysis to the corresponding acids (the latter may be further characterised as in Section IV,175) conversion into amides (Section IV,191), anihdes or p-toluidides (Section IV,100) and conversion into sohd esters (Section IV,183). 

Upon warming with 10-20 per cent, sodium or potassium hydroxide solution, no ammonia is evolved (distinction from primary amides). The base, however, is usually liberated upon fusion with soda lime (see experimental details in Section IV,175) and at the same time the acyl group yields a hydrocarbon. Thus benz-p-toluidide affords p-tolu-idine and benzene. 

Aceto-p-toluidide [103-89-9] M 149.2, m 146 , b 307 /760mm. Crystd from aqueous EtOH. 

The most extensive study of the effect of conditions upon the kinetics of bromination was made by Robertson et al.23l 279, who measured the rates of bromination of alkylbenzenes, acetanilide, aceto-p-toluidide, mesitylene, anisole and p-tolyl methyl ether in acetic acid at 24 °C. They found that at relatively high concentrations of bromine (A//40-M/100) the reaction is second-order in bromine, i.e. the rate equation is... 

Die Halbwertszeiten des Austauschs von N-p-Tolyl-glucosylamin, N-p-Tolyl-4.6-0-benzyliden-glucosylamin,N-p-Tolyl-3.4.5.6-tetrabenzoyl-glucosylamin und Glykolaldehyd-p-toluidid mit p-Toluidin imter-scheiden sich um GroBenordnungen (vgl. Tabelle 1). Nach 1. c. i7) ist der Mechanismus 35 39 - 40 - 41 - -42 - 37 oder 35 39 - -41 - -42 - ... 

Beckmann rearrangement of, 729,741 p-Benzoquinone, 745 Benzoylacetone, 865 o-Benzoylbenzoic acid, 728, 739 Benzoyl chloride, 791, 792 Benzoyl glycine, 584 Benzoyl peroxide, 807 determination of, 809 Benzoyl piperidine, 489, 492 P-Benzoylpropionic acid, 728, 737 P-Benzoylpropionitrfle, 911, 912 Benzoyl-p-toluidide, 582, 583 Benzyl acetate, 780, 783 Benzylacetophenone, 726, 734 Benzyl alcohol, 706,711, 811,812,884 N-Benzylamid es 394 table of, 395 ... 

Selenodiglycollic p-toluidide may be prepared from diseleno-diglycollic p-toluidide, or by treating chloraceto-p-toluidide with potassium selenide. The product melts at 217° to 218° C., is soluble in alcohol or hot acetic acid, sparingly soluble in chloroform or benzene, insoluble in water. Selenoxal-p-toluidide separates from dilute alcohol in long, red needles, M.pt. 165° to 166° C., soluble in alcohol, acetic acid, chloroform or benzene, insoluble in water. 

Preparation 276.—Benzoyl-p-toluidide p-Toluoyl-amide of benzene carboxylic add). 

Amino-2,3-dinitrotoluene large yel prisms 125.5-126 Hydrolysis with Na hydroxide 2,3-dinitro-p- toluidide ... 

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