Amino-anilides

Phosphorsaure-monoester-amide sind gegeniiber Alkoholen relativ inert [vgl. Bd. XII/2 (4. Aufl.), S. 270], jedoch reagiert z.B. Phosphorsaure-(2-amino-anilid)-(4-methoxy-phenylester) unter Kupfer(II)-chlorid Katalyse glatt mit Alkanolen unter Substitution des Amid-Rcstes (69-82%)124 ... 

Aryloxy-2,3-dihydro-lH-l,3,2-benzodiazaphosphol-2-oxide reagieren bereits bei 20° mit Wasser unter Ringoffnung zu Phosphorsaure-(2-amino-anilid)-arylester150 15 ... 

Wird in Gegenwart von Alkoholen in THF (24 Stdn./RiickfluB) gearbeitet, so werden in mittleren Ausbeuten Phosphorsaure-0-alkylester-(2-amino-anilide) gewon-... 

H-1,2-Diazepin 1 -Acetyl-3-methyl-E9d, 339 (Py-l-acetylimin/hv) Essigsaure -(4-amino-anilid) E18, 659 (N02 NH2)... 

Benzaldehyd 4-(Bis-[2-cyan-ethyl]-amino)- E3, 54 (H -+ CHO) Benzoesaure 2-Amino- -(4-amino-anilid) IV/lc, 597 Hydrazin... 

Aromatic amine produced,. mine salts anilides aromatic amino-carboxylic acids sulphanilic acid, sulphanilamide. 

Aromatic amines form addition compounds and complexes with many inorganic substances, such as ziac chloride, copper chloride, uranium tetrachloride, or boron trifluoride. Various metals react with the amino group to form metal anilides and hydrochloric, sulfuric, or phosphoric acid salts of aniline are important intermediates in the dye industry. 

Table 6-3. Resolution of amino acid derivatives on a MIP imprinted with L-phenylalanine anilide (L-PA).

TRIFLUOROACETYLATION OF AMINES AND AMINO ACIDS UNDER NEUTRAL, MILD CONDITIONS N-TRIFLUOROACET ANILIDE AND N-TRIFLUOROACETYL-l-TYROSINE... 

R=Me or COOEt) failed.2-Amino-4-phosphonobutanoic acid, the phosphonic acid analogue of glutamic acid, has been obtained in resolved forms by the action of papain, followed by aniline, on 2-benzoylamino-4-(diethoxyphosphinyl)butanoic acid when anilide occurs preferentially for the L- compound. Enantiomers of 4-amino-4-phosphonobutanoic acid were obtained by resolution... 

Direct thionation of amino acid derivatives has been achieved using P4S10. Direct thionation of anilide has been achieved with a mixture of P4S10 and anhydrous Na2C03 in THF.19 Selective thionation of amide has been achieved using P4S10 in THF under ultrasound irradiation. By-product is absent from the phosphorus pentasulfide thionation. Thionation of the amide with Lawesson s reagent is less selective (Scheme 4).20... 

This procedure may be used to prepare other substituted anilides. If one of the components is a solid, it can be dissolved in an excess of the other. For instance, 46 g. of 2-amino-5-nitroanisole in 285 ml. of hot ethyl bcnzoylacetate is passed through in 30 minutes, with a transformer setting of 70 volts then the column is rinsed with 50 ml. of the ester. The product crystallizes in the receiver and is... 

This subsection is devoted to the metabolic reactivity of the amide bond in anilides, i.e., compounds whose amino moiety is attached to an aromatic ring. Based on the nature of the acyl moiety, a number of classes of anilides exist, three of which are of particular interest here, namely arylacetamides, acylani-lides, and aminoacylanilides. The first group contains several analgesic-antipyretic drugs, the second A4-acyl derivatives of sulfonamides, and the third a number of local anesthetics. Particular attention will be paid to structure-metabolism relationships in the hydrolysis of these compounds. Cases where hydrolysis leads to toxification will be summarized in the last part of the chapter. 

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