Amines 3,5-dinitrobenzoyl chloride

Organic synthesis 10 [OS 10] 2x2 library from nitro- and dinitrobenzoyl chlorides and two amines... 

Nitrobenzoyl chloride and 3,5-dinitrobenzoyl chloride were each reacted with dl-1-phenylethylamine and 4-amino-l-benzylpiperidine using a phase-transfer reaction [23]. The amines were in the aqueous phase and the acid chlorides in the organic phase. By this means, a 2 x 2 library was created in one experimental run. 

Suitable reagents for derivatizing specific functional groups are summarized in Table 8.21. Many of the reactions and reagents are the familiar ones used in qualitative analysis for the characterization of organic compounds by physical means. Alcohols are converted to esters by reaction with an acid chloride in the presence of a base catalyst (e.g., pyridine, tertiary amine, etc). If the alcohol is to be recovered after the separation, then a derivative which is fairly easy to hydrolyze, such as p-nltrophenylcarbonate, is convenient. If the sample contains labile groups, phenylurethane derivatives can be prepared under very mild reaction conditions. Alcohols in aqueous solution can be derivatized with 3,5-dinitrobenzoyl chloride. 

An easily accessible DA CSP derived from L-A-(2-naphthyl)valine (80) was used to separate appropriately derivatized amines, amino alcohols and thiols, derivatization consisting of N-, O- and 5-acylation with 3,5-dinitrobenzoyl chloride or 3,5-dinitrophenyl... 

The r-donor phases (typically naphthyl-amino-acid derivatives covalently bonded to silica) require the analyte to contain a r-acceptor group such as the dinitrobenzoyl group. The dinitrobenzoyl group can easily be added to a wide range of compounds such as alcohols, amines and carboxylic acids using dinitrobenzoyl chloride, isocyanate or dinitroanaline, as already mentioned above. 

Amine 212 was also coupled with peptides [233], acetic anhydride [215, 234], dinitrobenzoyl chloride [235] or a ferrocene carboxylic add chloride [215, 236] in good yields. Reaction with dinitrochlorobenzene [237] or dinitrofluorobenzene... 

T rinitrobutylbenzomide, C11H12N4°7 mW 312.24, N 17.95%. Three isomers are discussed in the literature N-(n-Butyl)-N,3,5-trinitro-benzamide, CH3(CH2)3.N(N02).OC.C6H3(NO2)2, no props given was obtd as the residue from reaction of 3,5 dinitrobenzoyl chloride with the Na salt of N-nitrobutyl-amine(Ref 2) ... 

Dinitrobenzoyl chloride (DNBC) derivatization of alcohols, amines and... 

The first ionically bonded phase was presented by Pirkle it contained (/ )-3,5-dinitrobenzoyl phenylglycine [13]. The most commonly used 7t-acid moiety is the 3,5-dinitrophenyl group introduced by the reaction of 3,5-dinitrobenzoyl chloride (DNB-C1) on chiral selectors such as amino acids, amino alcohols, and amines. In addition, pentafluorobenzoyl derivatives have also been reported [14,15]. The 7r-basic phases are complimentary to the re-acidic phases. These CSPs include the presence of phenyl- or alkyl-substituted phenyl groups. Macaudiere et al. [9] designed a CSP containing both re-acidic and re-basic... 

Various derivatization reagents have been developed and used as labeling reagents for traces of primary and secondary aliphatic amines in HPLC, including OPA, 3,5-dinitrobenzoyl chloride,... 

Kirschbaum, J., Rebscher, K., Bruckner, H. (2000). Liquid chromatographic determination of biogenic amines in fermented foods after derivatization with 3,5-dinitrobenzoyl chloride. Journal of Chromatography, 881,517-530. http //dx.doi.org/ 10.1016/S0021 -9673(00)00257-0. 

The second method needs derivatization with either 3,5-dinitrophenyl isocyanate or 3,5-dinitrobenzoyl chloride which is followed by separation on a chiral acrylic polymer YMC A-K03 (a conjugated o-naphthylethyl amine, on a silica gel surface), Sumipax OA-4000, and/or TSK gel Enantio PI. 

Dinitrobenzamides of primary and secondary amines can be separated by column chromatography on alumina using a mixture of chloroform and benzene (for example, in the ratio 1 3) as eluent. The separation and the purity of fractions are controlled by paper or thin-layer chromatography. As primary and secondary amines react quantitatively with 3,5-dinitrobenzoyl chloride, while tertiary amines do not, the separation of amines and their purification can be easily performed on this basis. The preparation of derivatives is easy (see p. 334), both starting from free... 

Lewis (74f) reports the observation by Ijewis and Farrissey of a 7% increase in rate of the reaction between triethylamine deuterated in one ethyl group and methyl brosylate The effect is comparable to those observed on the base strength of a-deuterated amines (Table VII). It is less easy to understand Simon and Palm s (118) observation that introduction of tritium into methanol reduces the rate of its reaction with 2,4-dinitrobenzoyl chloride by 12%. To be sure, the reaction was carried out in alkaline solution, so that it may involve a pre-equilibrium. If so, the increased reactivity of tritiated methoxide ion should be offset by its smaller equilibrium concentration. Still the net effect is uncomfortably large. 

An example for this approach is the immobilization of (5 )-(-)-a-A-(2-naph-thyl)leucine, a 7t-donating group on silica. This chiral selector exhibits excellent recognition for 3,5-dinitrobenzoyl (DNB)- and 3,5-dintroanilido (DNAn)-deriva-tives. Amines and alcohols can be derivatized with DNB- or DNAn-chloride to the esters or carbamates and separated on the CSP, as shown by Pirkle for a wide variety of compounds [27]. 

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