Amide-formaldehyde-reaction-products

However, an exception must be made for those A-hydroxymethyl amides that derive from antimicrobial effective compounds having an amide configuration in the molecule, e.g. a-halogen-amides (introduction of a second toxophoric group into the molecule). 

Amides derive also from carbonic acid. The hemiamide of carbonic acid = carbamic acid (H2N-COOH) cannot be in existence it degrades spontaneously to CO2 and NH3. However, salts and esters of carbamic acid are more or less stable. The esters, H2N-COOR, are named urethanes. They react with ammonia to urea, the diamide of carbonic acid, (NH2)2C = 0. Urethanes and urea add readily formaldehyde forming N-hydroxymethyl or N,N -bis-hydroxymethyl derivatives which are formaldehyde releasing compounds. 

Carbondisulfide (CS2) reacts in analogy to CO2 with amines to dithiocarbamates (H2N-CSSR) (see 11. Carbamates) and thiourea (NH2)2C = S. The addition of formaldehyde leads to N- or S- hydroxymethyl derivatives, formaldehyde liberating substances. 

Chemical name Chemical formula Structural formula Molecular mass CAS-No. 

---

AMIDE-FORMALDEHYDE-REACTION-PRODUCTS 3.4.3. N-hydroxymethyl-ureas... 

Thermal Stability. Dimethyl sulfoxide decomposes slowly at 189°C to a mixture of products that includes methanethiol, formaldehyde, water, bis(methylthio)methane, dimethyl disulfide, dimethyl sulfone, and dimethyl sulfide. The decomposition is accelerated by acids, glycols, or amides (30). This product mixture suggests a sequence in which DMSO initially undergoes a Pummerer reaction to give (methylthio)methano1, which is labile and reacts according to equations 1—3. Disproportionation (eq. 4) also occurs to a small extent ... 

Pictet-Spengler cyclization of L-tryptophan with formaldehyde afforded the monochiral carboxylic acids 20a,b, whereas cyclization with acetaldehyde yielded the diastereomeric carboxylic acids 21a,b (23). Acids 20a,b with a hydrogen at C-1 are enantiomers, but acids 21a,b are diaste-reomers the cis isomer 21a was the major reaction product when the cyclization of L-tryptophan with acetaldehyde was carried out in the presence of sulfuric acid. Direct removal of the carboxy group in these acids is difficult, but it can be accomplished in several steps dehydration of the amides prepared from the acids with phosphorus oxychloride affords nitriles, and the nitrile group can be removed by reduction with sodium borohydride in pyridine-ethanol (31). 

The main reaction products of prebiotic chemistry were H2, H20, CH4, CO, C02, NH3, and N2. These compounds formed many intermediates including ions and radicals. The more important molecules that formed were formaldehyde HCHO, hydrogen cyanide HCN, phosphate ions, and cyan amide NH2CN. The final spectrum of products encompassed glycerol, glyceraldehyde - the parent compounds of sugars - carboxylic acids, amino acids, urea, guanidine, purines, and pyrimidines. As an example for the many possible interactions the formation of the nucleobase, uracil is shown in Fig. 2.1. 

Other complex mixtures involving Mannich reaction products of use as anti-rust additives in lubricating oils have included the reaction of fatty acids (RCO2H), nonylphenol, with diethylenetriamine or triethylenetriamine and aqueous formaldehyde. It would appear that the primary amine groups result in amide formation at 160-180°C and the residual secondary amine group then undergoes a Mannich reaction in the usual way with t-octyllphenol and... 

A -methoxymethyl-amines or-amides A -acetyloxymethyl-amines or -amides or A/, iV-dimethylfonnamide acetals, all react with phosphorus(III) esters in non-classical Michaelis-Arbuzov fashion. From these and similar reactions, quaternary salts of the type 186 have been isolated. The A-methylated dervative may be preformed or produced in situ in mixtures containing amide, formaldehyde and phosphite ester. The products of the reactions are A-acylated (acetyl, benzoyl, phthaloyl, pyridinecarbonyl or benzyloxycarbonyl) when derived from amides, or A,A-dialkyl derivatives from hydroxy (or methoxy)methylamines the use of Me2NCH(OMe)2 leads to dimethylaminomethyl-enebisphosphonic esters. Ivanov and coworkers have made a detailed study of the reactions which occur between phosphorus(III) amides Et2NPYZ and the substrates, RCONHOAc (Scheme 16). The reagent can attack the substrate by virtue of the nucle-... 

These urea derivatives are listed among the reaction products of amides and formaldehydes because urea is regarded as the diamide of carbonic acid. 

The heterocyclic N,S compounds Dazomet (Section 3.3.16) and Taurolin (Section 3.5.2.) can be regarded as formaldehyde releasing compounds therefore they are listed in Section 3. The A -hydroxymethyl derivative of 2-mercaptobenzothiazole (Section 3.4.10.2) is a formaldehyde releasing compound too and is described under Section 3.4, Reaction products of amides and formaldehydes . 

Ease of use in production. An important feature of each raw material in the paint production is the user friendly easy handling making formulated biocides a necessity. Safe, free flowing pumpable, non-flammable liquids with no agressive odors are preferred. A very important example is formaldehyde, which is as such a very aggressive, toxic substance, which can be replaced advantageously by reaction products with amines, alcohols or amides. 

Dioxo-imidazolidines, also called hydantoins, include the carbonamide structure, too, and therefore the corresponding N-hydroxymethyl compounds here are listed among the reaction products of amides and formaldehyde. The monohydroxymethyl compound is described for the sake of completeness the more active and important microbicide is the dihydroxymethyl compound 3.4.9. 

Indole (I) condenses with formaldehyde and dimethylamine in the presence of acetie acid (Mannich reaction see Section VI,20) largely in the 3-position to give 3 dimethylaminomethylindole or gramine (II). The latter reaets in hot aqueous ethanol with sodium cyanide to give the nitrile (III) upon boiling the reaction mixture, the nitrile undergoes hydrolysis to yield 3-indoleaeet-amide (IV), part of which is further hydrolysed to 3-indoleacetic acid (V, as sodium salt). The product is a readily separable mixture of 20 per cent, of (IV) and 80 per cent, of (V). 

Bisamides. Methylenebisamides are prepared by the reaction of the primary fatty amide and formaldehyde in the presence of an acid catalyst. AijAT-Methylenebisoleamide has been made via this route without the use of refluxing solvent (55). Polymethylenebisamides can be made from fatty acid, esters, or acid haUdes with diamines while producing water, alcohol, or mineral acid by-products. Eatty acids and diamines, typically ethylenediamine, have been condensed in the presence of NaBH and NaH2P02 to yield bisamides (56). When stearic acid, ethylenediamine, and methyl acetate react for 6 h at... 

The addition of copper to a boiling solution of benzenesulphonyl azide in methanol gave benzenesulphonamide 18 (80%) as the major product together with minor amounts of methylenebis(benzenesulphon-amide) 22 and 1,3,5-tris (benzenesulphonyl) hexahydro-s-triazine 23, resulting from condensation of 18 with the formaldehyde formed in the reaction 33>. Cuprous chloride was even more effective, but cuprous... 

Hexamethylolmelamine can further condense in the presence of an acid catalyst ether linkages can also form (see Urea Formaldehyde ). A wide variety of resins can be obtained by careful selection of pH, reaction temperature, reactant ratio, amino monomer, and extent of condensation. Liquid coating resins are prepared by reacting methanol or butanol with the initial methylolated products. These can be used to produce hard, solvent-resistant coatings by heating with a variety of hydroxy, carboxyl, and amide functional polymers to produce a cross-linked film. 

---