Butyric amide

A/-(2,4-dimethyl-phenyl)-3-oxo-butyr amide [97-36-9] mp 89 orange and yellow pigments... 

Cellulose-acetate-butyrate resin Poly(amide-imide)... 

Whereas primary amides such as butyric acid amide, on heating to 140-150 °C with triethylsilane 84b and ZnCl2, give, e.g., 78% butyronitrile 1853 and 95% HMDSO 7 [79], the secondary amide benzanilide is readily converted into 90% O-triethylsilyl imino ether 1854 [80] whereas the tertiary amide N,N-diethylacetamide... 

Figure 15.14 The NHS ester of a pyrene butyric acid derivative can be used to modify a carbon nanotube by adsorption of its rings onto the surface of the tube. The NHS ester groups then can be used to couple amine-containing molecules to form amide bonds.

Succinimidyl-4-(p-maleimidophenyl)butyrate (SMPB), is a heterobifunctional analog of MBS containing an extended cross-bridge (Chapter 5, Section 1.6). The crosslinker has an amine-reactive NHS ester on one end and a sulfhydryl-reactive maleimide group on the other. Conjugates formed using SMPB thus are linked by stable amide and thioether bonds. 

In search of a convenient procedure for preparing diazo substrates for the cycloaddition to Cgg, Wudl introduced the base-induced decomposition of tosyl-hydrazones [116]. This procedure allows the in situ generation of the diazo compoimd without the requirement of its purification prior to addition to Cgg. Since they are rapidly trapped by the fullerene, even unstable diazo compounds can be successfully used in the 1,3-dipolar cycloaddition. In a one-pot reaction the tosyUiydrazone is converted into its anion with bases such as sodium methoxide or butylHfhium, which after decomposition readily adds to Cgg (at about 70 °C). This method was first proven to be successful with substrate 142. Some more reactions that indicate the versatility of this procedure are shown in Table 4.4. Reaction of 142 with CgQ under the previously described conditions and subsequent deprotection of the tert-butyl ester leads to [6,6]-phenyl-C5j-butyric acid (PCBA) that can easily be functionalized by esterification or amide-formation [116]. PCBA was used to obtain the already described binaphthyl-dimer (obtained from 149 by twofold addition) in a DCC-coupling reaction [122]. 

H, G. Walker, R. Levine and R. F. Kibler The Carbethoxylation of Ethyl Phenylacetate and of Ethyl-a-Phenyl-n-butyrate using Sodium Amide. J. Amer. chem. Soc. 68, 672 (1946). 

Cyclization of 2-aminonicotinic acid with butyric anhydride gave the 2-propyM//-pyrido[2,3-4 [l,3]oxazin-4-one 698 <2004W02004039774>, while the 2-isobutyl analogue 699 was prepared via the cyclization of amide 697, obtained from acylation of 2-aminonicotinic acid with isovaleryl chloride, in AC2O at 120°C <2003W02003103575>. 

A benzazepine that includes the same (3-ketoamide array as piroxicam (Chapter 11) retains NSAID activity. Oxidation of benzothiapinone (5-1), obtainable by cycli-zation of 4-(4-chlorophenylthio)-butyric acid, with hydrogen peroxide gives the corresponding sulfone (5-2). This is then converted to its enamine (5-34) by reaction with pyrrolidine. Condensation of the intermediate with 3,4-dichorophenylisocyanate (5-4) leads to the amide (5-5). Hydrolysis with an aqueous acid cleaves the enamine function to give the keto-amide and thus enolicam (5-6) [6]. 

Later investigators alcoholyzed imidate salts of other monobasic acids to obtain ortho esters of acetic [13, 14], propionic [15], butyric, valeric, caproic, isocaproic, benzoic [16], and phenylacetic acids [17]. For the latter alcoholysis reactions, the reaction time varies from a few days for the production of methyl orthopropionate to six weeks for ethyl orthobenzoate. McElvain reported that the reaction time is drastically cut by carrying out the reaction in boiling ether [18] or petroleum ether [19]. These conditions provide a reaction temperature below the decomposition point of the imidate salt to the amide. 

Azidobutyric Acid Amide. See under Butyric Acid Amide and Beil 2, 287 299 Azidobutyric Acid Azide. See Azidobutyryl-azide... 

Azidobutyramide, C4H8N40 128.14, N 43.73%-Two isomers are known 2-Azido-n-butyric-l-amide, CH3.CH2.CH(N3).CO.NH2, ndls(from benz+ petr eth), mp 38-9°(dl-fbrm) ndls(from benz), mp 59°(l form) and 2-Azidn-iso-butyr-l-amide or 2-A zido-2-methyl-propion-I-amide, (C1I )2C(N3 ).-CO.NH2, rectangular pltlts, mp 93-4°. Other props methods of prepn are given in Refs 1 2 Refs l)Beil 2,287,299 2)M.D.Forster R. 

Propylaminobutyric acid dimethyl amide is dissolved in benzene and while cooling, crotonic acid chloride is added and mixed. Then, reaction mixture is filtered and freed from benzene to give 2-(N-propyl-crotonylamido)butyric acid dimethyl amide, melting point 128°-130°C. 

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