Benzoyl amino compounds

Benzoyl Amino Compounds.—Benzoyl chloride also reacts with ammonia, aniline and amino acids yielding acid amide compounds. 

In the Schotten-Baumann method of benzoylation, the hydroxyl- or amino-compound (or a salt of the latter) is dissolved or suspended in an excess of 10% aqueous sodium hydroxide solution, a small excess (about 10% more than the theoretical amount) of benzoyl chloride is then added and the mixture vigorously shaken. Benzoylation proceeds smoothly under these conditions, and the solid benzoyl compound, being insoluble in water, separates out. The sodium hydroxide then hydrolyses the excess of benzoyl chloride, giving sodium... 

Multifunctional Hydroxy, Mercapto, and Amino Compounds. These are used to cross-link halogenated polymers. Depending on the labihty of the halogen, the cross-linking agents can be capped to reduce reactivity or used in combination with accelerators to increase the rate of reaction. Benzoyl capping is common with hydroxy and mercapto compounds forming the carbamate by reaction with one equivalent of carbon dioxide is used with diamines. 

Industrially important pigments typically show the following substitution pattern A represents an ethoxy group, B represents an acetylamino or a benzoyl-amino moiety, and X is a chlorine atom or an NHCOCH3 function. The commercially most important compound 115, however, is somewhat of an exception in that A and E or B represent the heterocyclic moiety, which formally results... 

Three synthetic approaches for benzopyrones have been developed that use Gly as starting material. Hippuric acid was transformed with acetic anhydride into 2-phenyl-5(4//)oxazolone or further into its 4-ethoxy-methylene derivative, then reacted with cyclic 1,3-dicarbonyI compounds (such as like dimedone) to form 100 [90LA501 92H(33)843]. On the other hand, when hippuric acid was transformed into methyl 2-benzoyl-amino-3-dimethylaminopropenoate, it reacted with resorcinol to give a 7-hydroxybenzopyrone derivative (89JHC1273). 

Similarly, reaction of 2-dimethylaminomethylene-3-oxoalkanoates or 2-di-methylaminomethylene-1,3-cyclohexanediones with 2-phenyl-5(4/7)-oxazolone 146, generated in situ from hippuric acid, affords 6-substituted 3-(benzoyl-amino)-2-oxo-2//-pyran-5-carboxylates 204 and 3-(benzoylamino)-7,8-dihydro-2//-l-benzopyran-2,5(6//)-diones 206, respectively. These compounds showed strong local anesthetic activity (Scheme 7.62). ... 

The commonly encountered compounds in this class are the formyl, acetyl and benzoyl derivatives. The formation of the N-formyl compound is readily accomplished by heating the amino compound with formic acid in the presence of acetic anhydride.223 Alternatively, formic acid in the presence of dicyclohexl-carbodiimide (DCC) in pyridine solution is a suitable method for the protection of amino acid esters.224... 

Some compounds like [[[(aminooxopyrimido[5,4-6][l,4]thiazin-6-yl)alkyl]benzoyl]amino]pen-tandioates (279) have been disclosed as inhibitors of the enzyme glyrinamide ribonucleotide formyl transferase (GARFT) <93USPl086i>. 

The diazepinone (127) reacted with benzoyl chloride to give the A,Ar -dibenzoyl derivative137 and was brominated in acetic acid at 20°.138 Compounds 127 and 128 undergo the bis-semidine inversion when heated with 3% hydrochloric acid.117 The thione (128) is converted in high yield into the methylmercapto diazepine (126, R = SCH3) by reaction with methyl iodide in tetrahydrofuran.129 The thione does not react with amines, but the 6-methylmercapto compound on heating with amines or amine hydrochlorides gave rise to the 6-amino compounds (126, R = NR R")120 A number of these amino derivatives have exhibited some medicinal activity. With -butanol the 6-methylmercapto compound is quantitatively converted into 127.120... 

Good evidence for nitration at the 3-position was provided by Clayton and Kenyon. l-Benzoyl-2,5-dimethyl-4-azaindole was nitrated in 60 % yield, and followed with potassium permanganate oxidation in aqueous acetone gave 3-benzamido-6-methylpicolinic acid. Alkaline hydrolysis of the nitration product gave 3-nitro-2,5-dimethyl-4-azaindole (85% yield), which was also obtained by direct nitration of 2,5-dimethyl-4-azaindole in low yield. In addition, reduction gave the 3-amino compound, which was identical to that obtained by catalytic reduction of the product formed by coupling the azaindole with benzenediazonium chloride. 

From this virtual screening, 31 compounds (compound e. Fig. 16) have been identified to show the activity at IC50 < 10 xM. Among these a thiazole analogue, 2-(3-benzonitrile)amino-5-benzoyl-thiazole (compound f. Fig. 16), has been found to be the most active compound with an IC50 of 40 nM for the mouse Y5 receptor and even showed activity in a mice feeding model at... 

Benzoyl-p-aminophenylarsinie acid was first described in 1906, and prepared by the benzoylation of sodium p-aminophenylarsinatc, using benzoyl chloride and aqueous sodium hydroxide. Replacing the benzoyl chloride by o-, m- or p-nitrobenzoyl chloride. King isolated o -, m -, and p -mononitrobenzoyl-p-aminophenylarsinic acids respectively, which in turn were reduced to the corresponding amino-compounds in yields of 60 to 86 per cent. ... 

Benzoylation.—The introduction of the benzoyl radical for alcoholic hydrogen is termed benzoylation corresponding to acetylation or th introduction of the acetyl radical in the aliphatic compounds. The action of benzoyl chloride is more moderate than that of acetyl chloride and furthermore the products are often crystalline and, therefore, readily identified. These facts often make it more desirable to ben-zoylate an hydroxyl or amino compound than to acetylate it, when it is necessary to know whether an unknown substance is an alcoholic hydroxyl compound or an amino compound, and how many of such groups are present (p. 318). 

For the introduction of the benzoyl group (benzoylation) the procedure generally adopted is to use benzoyl chloride in dilute (10 per cent) alkaline solutions. Since benzoyl chloride reacts slowly with water at room temperature, the amino compound reacts fairly rapidly when shaken with it. The hydrogen chloride produced in the acylation is removed by the alkali. This method is known as the Schotten-Baumann reaction. The benzoyl derivatives nearly always crystallize well. The product is recrystallized to remove adsorbed and occluded impurities. If the derivative does not crystallize well, then a substituted benzoyl chloride is used, for example, p-nitrobenzoyl chloride. It will be recalled that for the characterization of the alcohols use was made of 3, 5-dinitrobenzoyl chloride. 

Hydroxylation, followed by selective benzoylation, afforded compound 12. The amino group was introduced by oxidation of the free hydroxyl group, and conversion to the oxime 14, followed by reduction, gave - after N-acetylation -lincosamine 15 in its protected form as well as its 6-epimer 16. 

Pyromucyl chloride a-furfuranecarboxyl chloride) is prepared by heating pyromucic acid with thionyl chloride (5 parts) on the water-bath and fractionating the residue. The yield is quantitative. The chloride reacts readily with hydroxyl and amino compounds, under conditions similar to those employed in the case of benzoyl chloride. As a rule the products are somewhat more soluble than... 

The acetyl and benzoyl derivatives have been used as well as the formyl derivatives in the synthesis of various amino compounds employing acetamido , benzamido and formamido malonate respectively. In the synthesis of the 64 possible ribotrinucleotides which are derived from the four major ribonucleotides, the amino group of two of the heterocyclic bases, adenine (1) and cytosine (2), was protected by an acetyl or a benzoyl group The acyl derivatives in this... 

The benzoyl derivatives of some amino-compounds (e.g. amino-acids) are soluble in the alkaline reaction medium they may be precipitated together with benzoic acid (from the reagent) by careful acidification. The derivative may be removed by extraction of the product with benzene or light petroleum (b.p. 40-60°). 

Another approach for the coupled racemization step has been used for compounds having an acidic hydrogen on the stereocenter. Examples of such compounds are chiral acyl donors such as a-substituted esters which are prone to base-catalyzed racemization via an enolate intermediate. This approach has been frequently used and a few examples will be given here to illustrate the utility (Scheme 11). The first examples involve oxa-zolinones where it was found that porcine pancreatic lipase and lipase from Aspergillus sp. exhibited opposite enantiopreferences [106,107]. The remaining oxazolinone was spontaneously racemized via the enolate intermediate and both (l)- and (D)-iV-benzoyl amino acids could be produced this way in high chemical and optical yields. The p Ka values of thio esters are lower than those of oxo esters [108]. This has been used in the lipase-... 

Phosphorus-nitrogen compounds containing alkylated amino groups can be cleaved by fluormatmg agents Phenyldifluorophosphine is formed from the reaction of A,MA, lV -tetramethylphenylphosphonous amide and benzoyl fluoride [79] (equation 17). 

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