6326-73-4

Upstream product

• 64-17-5 ethanol 
• 2014-79-1 diphenyl methylphosphoramidate 
• 70160-21-3 di-p-methoxyphenyl N-methylamidophosphate 
• 70138-25-9 di-m-nitrophenyl N-methylamidophosphate 
• 13294-10-5 diethyl N-acetyl-N-methylphosphoramidate 
• 100-52-7 benzaldehyde 
• 814-49-3 diethyl chlorophosphate 

Downstream Products

• 2404-03-7 diethyl N,N-dimethylphosphoramide 
• 73392-27-5 2-(diethoxyphosphinyl)-N-methyl-2-phenylketenimine 
• 6830-83-7 N-methyl-pivalamide 
• 82134-81-4 diethyl benzoylmethylphosphoramidate 
• 88070-48-8 N-methylbenzamide 
• 93-89-0 benzoic acid ethyl ester 
• 23825-32-3 N-benzoyl-N-methylbenzamide 

Relevant academic research and scientific papers

A new nitrogen-to-oxygen phosphoryl migration

The reaction of diethyl N-acetyl-N-methylphosphoramidate 1 with aldehyde in the presence of LDA at -70°C results in the formation of the unstable oxyanion 6 which undergoes intramolecular rearrangement involving migration of a phosphoryl group from nitrogen to oxygen affording an amide anion 8. Subsequent proton transfer in 8 followed by elimination of phosphate anion provides the respective α,β-unsaturated N-methylcarboxamide 4. The formation of considerable amounts of diethyl N-methylphosphoramidate 5 is also always observed.

PHOSPHORIC-CARBOXYLIC IMIDES. III. THE BENZOYLATION OF N-METHYLDIETHYLPHOSPHORAMIDATE AND RELATED ANIONS

The synthetic route to mixed phosphoric-carboxylic imides (1) via the N-acylation of phosphoramidates was investigated.The reaction of PhC(O)X(X = Br, Cl, F) with conjugate base of (EtO)2P(O)NHMe (2) yields three products: PhCO2Et (3), PhC(O)NHMe (4) and (PHCO)2NMe (5). (4) and (5) are formed via the initial rapid formation of (1), while (3) results from the ElcB raction of (2).The attack of various nucleophilic species at mixed imide (1) was studied, and the possible mechanisms of the P-N bond cleavage, followed by the transfer of nitrogen from phosphoryl to the carbonyl centre, are discussed.

Phosphoric-Carboxylic Imides. V. Reaction with Grignard Reagents

Mixed phosphoric-carboxylic imides were shown to react with Grignard reagents exclusively at the carbonyl centre.

SOLVOLYSIS OF DIPHENYL AMIDOPHOSPHATES IN AQUEOUS ALCOHOLIC MEDIA

Influence of substituent on the reaction rate of the alkali-catalyzed solvolysis of the studied compounds set has been followed.The activation entropy has also been determined.The reaction products have been identified, and their concentration ratio has been determined.The reaction selectivity is mostly influenced by sterical effects in the substrate molecule.The results obtained agree with the SN2 mechanism.