67264-80-6Relevant academic research and scientific papers
Formation of acrylanilides, acrylamides, and amides directly from carboxylic acids using thionyl chloride in dimethylacetamide in the absence of bases
Cvetovich, Raymond J.,DiMichele, Lisa
, p. 944 - 946 (2012/12/23)
A general one-pot procedure is described that rapidly converts acrylic acid to anilides upon sequential treatment of the acid in dimethylacetamide (DMAC) with thionyl chloride and stoichiometric amounts of anilines in 88-98% yields, with DMAC offering rate and stability advantages over the use of DMF. The use of DMAC was extended to other organic acids in forming anilides. Benzylamine amides can also be formed using stoichiometric amounts of benzylamine and brought to completion by warming in the absence of additional base. In addition, it was shown that tert-butylamides can be easily formed with the addition of excess tert-butylamine at 20 °C.
A New Route to N-Monosubstituted Thioamides Utilizing Phosphoramidothionates as Reagents for the Thioamidation of Carboxylic Acids
DeBruin, Kenneth E.,Boros, Eric E.
, p. 6091 - 6098 (2007/10/02)
Several N-monosubstituted thioamides have been synthesized from the corresponding carboxylic acid chlorides and primary amines by a new procedure.The procedure utilizes a commercially available and inexpensive organophosphorus reagent (dimethyl chlorothiophosphate) to derivatize the amine, form the carboxamide bond, and accomplish the thionation of the carbonyl by an intramolecular rearrangement.The phosphoryl group is then cleaved from the resulting thiocarbonyl phosphoryl mixed imide by a simple hydrolysis.Thioamides (RCSNHR') containing a variety of functionality(R= simple alkyl, phenyl, bulky alkyl, cycloalkylalkyl, α,β-unsaturated, and alkyl with remote keto, ester, or amide carbonyl groups; R'= methyl, benzyl, allyl) have been prepared by this method in generally high overall yields (50-80 percent).Competing thionation of remote carbonyl groups or epimerization of a chiral center containing a proton α to a ketone group was not observed.
1H NMR SPECTRA OF SOME JUVABIONE ANALOGUES
Mahajan, R. K.,Gupta, Neelam,Uppal, Satinder K.
, p. 690 - 696 (2007/10/02)
A number of aromatic aza-analogues of juvabione and dehydrojuvabione have been synthetized by treatment of substituted benzylamine with 3-methylbutanoyl chloride and 3-methyl-2-butenoyl chloride.Reaction of substituted phenoxyacetyl chlorides with isoprop
A CONVENIENT METHOD FOR THE SYNTHESIS OF CARBOXAMIDES AND PEPTIDES BY THE USE OF TETRABUTYLAMMONIUM SALTS
Watanabe, Yutaka,Mukaiyama, Teruaki
, p. 285 - 288 (2007/10/02)
Various carboxamides and peptides are prepared in good yields by treatment of free acids and amines in H2O-dichloromethane or aqueous THF with bis(o-nitrophenyl) phenylphosphonate in the presence of tetrabutylammonium hydrogen sulfate or bromide.Carboxylic esters are also successfully converted to amides via carboxylate salts in one-pot.
