N-alkyl formamides

Note that some N-alkyl-formamides such as dimethylformamide, are also liquid,... 

The Leuckart reductive animation of carbonyl compounds with ammonium formate or formamide was found to benefit strongly, when the reaction was carried out under solvent free conditions with microwave irradiation. Yields of N-alkylated formamides of up to 97% were produced in reaction times of about 30 min, as compared to thermal... 

Hydrogenation of isocyanates using 10% palladium-on-carbon catalyst has also been used to prepare N-alkyl formamides (3). 

The N-alkylation of amides followed by hydrolysis furnishes a good route for making secondary amines. The formyl, acetyl, and aryl-sulfonyl " derivatives of amines are best suited for alkylation (method 358). Hydrolysis is accomplished by refluxing concentrated hydrochloric acid alone or in acetic acid. N-Alkyl-formamides prepared by the addition of olefins to nitriles (method 355) are hydrolyzed with aqueous alkali. Similar hydrolytic procedures... 

The cation plays an important role in the electrcKhemical formation of the commercially important mono- and disubstituted N-alkyl formamides from CO in... 

Additions of aryl- or alkyllithium reagents to N-silylated formamides 508 give the imines 509 in 55-80% yield [90, 91] some of these imines can subsequently be converted into the corresponding //-lactams by reaction with enolates of alkyl butyrates [92]. Conversion of N-silylated butyrolactam 388 into cyclic Schiff bases such as 390, by reaction with methyl- or butyllithium, via O-silylated butyrolactam 389, is discussed in Section 4.8 (Scheme 5.28). 

Die Umwandlung von 1-Brom-alkanen in die entsprechenden 1-Amino-alkane gelingt in guten Ausbeuten auch durch Reaktion mit Kalium-cyanat und Ethanol in Dimethyl-formamid und alkalische Hydrolyse der zunachst gebildeten N-Alkyl-carbamidsaure-ethylester2. 

Applications of oxaziridine rearrangements in asymmetric syntheses have been reviewed,596 and the formation of N,N-disubstituted formamides (462) on sodium perborate oxidation of alkyl (V-arylal dimines (460) has been rationalized597 in terms of an intermediate oxaziridine (461) that rearranges via acid-catalysed O—N cleavage. 

For the preparation of Nd-BR with narrow MMDs a catalyst system which comprises five components is applied Nd-salt/electron donor add-itive/aluminum based halide donor/alumoxane/aluminum (hydrido) alkyl. The following additives are recommended in order to improve the solubility of the Nd salt acetylacetone, tetrahydrofuran, pyridine, N,N-dimelhyl-formamide, thiophene, diphenylether, triethylamine, organo-phosphoric compounds and mono- or bivalent alcohols. The catalyst components are prereacted for at least 30 seconds in the temperature range of 20-80 °C and catalyst aging is preferably performed in the presence of a small amount of diene [397,398]. 

Abb. 7.16. Ritter reaction part I (cf. Fig. 7.17) SN1 reaction between a tertiary alcohol and a nucleophile containing C=N, with hydrogen cyanide acting as the nucleophile. Under reaction conditions the C=N group is tert-alkylated at the N atom and hydrated at the nitrile nitrogen leading to the formation of an W-tert-alkyl-formamide (B). 

The reaction is not limited to DMF, but is applicable to compounds of the general formula R CCNR R-, in which R H or alkyl, and R = H, alkyl, or aryl, but not both = H. Particularly high yields of substituted aminoanthraquinones arc obtained from l-chloroanthraquinouc using N,N-diethylformamide, N-methyl-formamide, and N,N-dimcihylacctamide. 

Hence, a cationic, hposome-based targeted gene dehvery system is a better method under in vivo conditions. Recently, we synthesized a novel marmosylated cholesterol derivative, cholesten-5-yloxy-N-(4-((1 -imi no-2 - D-thiomaimosylethyl) ami no) -alkyl)formamide (Man-C4-Chol), for mannose receptor-mediated gene transfection to macrophages [50-53], which are known to express large numbers of mannose receptors on their surface. In primary cultured mouse peritoneal macrophages, pDNA, when complexed with Man-C4-... 

N-alkylamides different from formamides exclusively give rise to a-N-amidoalkyla-tion. Most of the study was accomplished with N-alkylacetamides because only the N-alkyl groups are involved in the substitution. The C—H bond in a to the carbonyl group can be also abstracted with some ease owing to the resonance stabilization 19)... 

Secondary1005,1031-1033 and tertiary amines1021,1029 1033-1035 are obtained analogously from ketones, by using the amine formate or jV-alkyl- or N,N-dialkyl-formamide in place of ammonia (or ammonium formate) or formamide. In this way iV-methyl- and iV,iV-dimethyl-cyclohexylamine are obtained from cyclohexanone and formic acid by methyl- and dimethyl-formamide, respectively, whereas formamide and formic acid give cyclohexylamine.1033... 

Die Aminierung mit Tetrakis-[dimethylamino]-titan gelingt beim Dimethylform-amid534,53s, auf tert. Formamide mit hoheren N-Alkyl-Resten wurde die Synthese offenbar nicht ausgeweitet. 

Watkinson [1988] lists some surfactants used for their dispersing action in organic liquids. He includes amongst them organic and metal sulphonates metal phenolates metal dialkyl dithiophosphates sodium dialkyl sulphosuccinates polyoxyethylene alkyl and alicyclic amines monethanol ammonium phosphate salts co-polymers of N-substituted formamide fatty acid phosphates... 

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