35123-06-9

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 69, p. 1911, 1947 DOI: 10.1021/ja01200a020Tetrahedron Letters, 16, p. 1731, 1975

InChI:InChI=1/C5H11NO2/c1-4(7)5(8)6(2)3/h4,7H,1-3H3

Upstream product

• 97-64-3 ethyl 2-hydroxypropionate 
• 124-40-3 dimethyl amine 
• 547-64-8 methyl lactate 
• 19432-30-5 Brenztraubensaeuredimethylamid 
• 13372-32-2 5-methyl-4-oxo-1,3-dioxolane 
• 849585-22-4 LACTIC ACID 
• 95-96-5 D,L-lactide 
• 758-96-3 N,N-dimethyl-propanamide 

Downstream Products

• 2680-03-7 N,N-Dimethylacrylamide 
• 193806-12-1 (R)-2-hydroxy-N,N-dimethylpropanamide 
• 31502-31-5 (S)-N,N-dimethyl lactamide 
• 1296198-59-8 C₁₁H₂₁NO₂ 
• 6280-18-8 DL-2-acetoxy-propionic acid dimethylamide 

Relevant academic research and scientific papers

METHOD FOR PREPARING ALKYL LACTATE AND A METHOD FOR PREPARING LACTAMIDE USING THE SAME

This disclosure relates to a method for preparing alkyl lactate with high yield and high selectivity, comprising the step of reacting glycerol with water or alcohol in the presence of a catalyst. In addition, the present invention provides a method for efficiently preparing lactamide using the alkyl lactate.

Process For Making Amides

Provided are processes for making an amide of a carboxylic acid by reacting an amine of the formula (I) [in-line-formulae]H—NR1R2 ??(I)[/in-line-formulae] wherein R1 and R2 are the same or different, R1 comprising a C1-C4-alkyl, and R2 comprising hydrogen or a C1-C4-alkyl, the amine having a lower boiling point than water, with a carboxylic acid with at least 3 carbon atoms per molecule, said carboxylic acid optionally comprising at least one alcoholic hydroxyl group per molecule, and selecting a molar ratio of amine to carboxylic acid in the range of from 1.5:1 to 1:1. The reaction step occurs under temperature and pressure conditions at which water and amine according to formula (I) are gaseous, and in a single reactor,the water formed together with any unreacted amine is distilled off, any unreacted amine is separated from the water and said the unreacted amine is reintroduced into the reaction mixture.

PROCESS FOR MAKING AMIDES

Process for making an amide of a carboxylic acid by reacting an amine of the formula (I) H-NR1R2, the integers being defined as being equal or different, R1 being selected from C1-C4-alkyl, R2 being selected from hydrogen and C1-C4-alkyl, R1 and R2 being combined in a way that amine according to formula (I) has a lower boiling point than water, with a carboxylic acid with at least 3 carbon atoms per molecule, said carboxylic acid optionally bearing at least one alcoholic hydroxyl group per molecule, selecting a molar ratio of amine according to formula (I) to carboxylic acid in the range of from 1.5 : 1 to 1 : 1, comprising the following measures: (a) reacting amine according to formula (I) with said carboxylic acid at temperature and pressure conditions at which water and amine according to formula (I) are gaseous, wherein the reaction (a) is performed in a single reactor, (b) distilling off the water formed, together with unreacted amine according to formula (I), (c) separating unreacted amine according to formula (I) from the water and (d) re-introducing said amine according to formula (I) into the reaction mixture in measure (a).

METHOD OF PREPARING DIALKYL LACTAMIDES

A method of preparing dialyl lactamides. The method of preparing dialkyl lactamides includes preparing ammonium lactate by reacting at least one compound selected from the group consisting of lactic acid and esters thereof with at least one amine compound, preparing dialkyl lactamides by heat-treating the ammonium lactate, and adding at least one of a polymerization inhibitor and an anti-polymerization agent to a reaction mixture of at least one of the preparing of the ammonium lactate and the preparing of the dialkyl lactamides.

ETHER-AMIDE COMPOUNDS AND USES THEREOF

Novel ether-amide compounds are described. Uses of the compounds, in particular as solvents, for example in phytosanitary formulations are also described.

Method For Producing Amides In The Presence Of Superheated Water

The invention relates to a method for producing carboxylic acid amides, according to which at least one carboxylic acid of formula (I) [in-line-formulae]R3—COON ??(I)[/in-line-formulae] wherein R3 is hydrogen or an optionally substituted hydrocarbon radical comprising between 1 and 50 carbon atoms, is reacted with at least one amine of formula (II) [in-line-formulae]HNR1R2 ??(II)[/in-line-formulae] wherein R1 and R2 are independently hydrogen or an optionally substituted hydrocarbon radical comprising between 1 and 100 C atoms, to form an ammonium salt, and said ammonium salt is reacted in the presence of superheated water, under microwave irradiation, to form a carboxylic acid amide.

Tribromogermyl monochelates - Derivatives of N,N-disubstituted 2-hydroxycarboxylic amides

Reactions of GeBr4 with N,N-dimethyl-2- trimethylsiloxypropionamide (2a), (S)-2-trime-thylsiloxypropionpyrrolidide ((S)-2b), and N,N-dimethyl-O-(trimethylsilyl)mandelamide (2c) afforded pentacoordinated neutral (O,O)-monochelates, viz., N,N-dimethyl-2-tribromoger- myloxypropionamide (3a), (S)-2-tribromogermyloxypropionpyrrolidide ((S)-3b), and N,N-dimethyl-O-(tribromogermyl)mandelamide (3c), respectively. X-ray diffraction study was performed for tribromides 3a, (S)-3b, and 3c, as well as for the N,N-dimethylmandelamide (1c) described earlier. According to the X-ray diffraction data, the Ge atom in tribromides 3a, (S)-3b, and 3c is pentacoordinated and has trigonal bipyramidal configuration with two halogen atoms and oxygen atom of the ether group in the equatorial positions and the halogen atom and the amide oxygen atom in the axial fragment, the bonds in which are somewhat longer as compared to the analogous bonds in tetracoordinated Ge compounds.

FORUMLATIONS

This invention relates to the use of lactamide compounds of formula (I): CH3CH(OH)C(=O)NR1R2, where R1 and R2 are each independently hydrogen; or C1-6 alkyl, C2-6 alkenyl or C3-6 cycloalkyl, each of which is optionally substituted by up to three substituents independently selected from phenyl, hydroxy, C1-5 alkoxy, morpholinyl and NR3R4 where R3 and R4 are each independently C1-3 alkyl; or phenyl optionally substituted by up to three substituents independently selected from C1-3 alkyl; or R1 and R2 together with the nitrogen atom to which they are attached form a morpholinyl, pyrrolidinyl, piperidinyl or azepanyl ring, each of which is optionally substituted by up to three substituents independently selected from C1-3 alkyl, in formulations to reduce the toxicity associated with other formulation components; to the use of certain lactamide compounds as solvents, especially in formulations, particularly in agrochemical formulations and in environmentally friendly formulations; to novel lactamide compounds; and to processes for preparing lactamide compounds.

Preparation of acrylic acid derivatives from alpha-or beta-hydroxy carboxylic acids

The invention is directed to a process for the preparation of α,β-unsaturated acids, esters and amides from α- or β-hydroxycarboxylic acids or esters or precursors in high yields and high selectivity. The α,β-unsaturated acids or esters are optionally prepared in the presence of specific dehydration and/or esterification catalysts. The α,β-unsaturated amides or substituted amides are prepared optionally in the presence of a dehydration and/or amidation catalyst. The source of α- or β-hydroxycarboxylic acids or precusor is preferably from a renewable resource. The precursor is defined herein.

Solvolytic Elimination Reactions of Tertiary α-CSNMe2-Substitutedd Systems

The tertiary benzylic α-CSNMe2-substituted p-nitrobenzoates and trifluoroacetates of general structure Ar(CH3)C(CSNMe2)(OCOR), 7 and 8, solvolyze to give exclusively elimination products H2C=C(CSNMe2)Ar.A Hammett study gave a nonlinear correlation.Variation in rate with solvent ionizing power was small for the unsubstituted trifluoroacetate derivative of 8, and the β-CD3 isotope effect on rate was negligible.There is, however, a large isotope effect (2.5-2.8) in formation of the elimination product when Ph(CH2D)C(CSNMe2)(OCOCF3) solvolyzes.It is concluded that an intermediate must be involved sine the product-determining step and the rate-determining step have differing isotope effects.The likely intermediate is an α-CSNMe2-substituted cation as an ion pair), despite the fact that the reaction has few characteristics of a typical E1 reaction.Tertiary noorbornyl, cyclohexyl, and 2-propyl α-CSNMe2-substituted systems also react to give exclusively elimination products at rates far in excess of α-CONMe2 analogues.It is suggested that α-CSNMe2 cations are also intermediates and that these cations undergo proton loss at an early ion pair stage.These cations are proposed to derive substitantial stabilization by charge delocalization onto sulfur of the thiocarbonyl group. By way of contrast, the secondary system CH3CH(CSNMe2)(OCOCF3), 25, solvolyzes to give mainly a rearranged product CH3CH(CONMe2)(SCOCH3) via a KΔ mechanism involving neighboring thiocarbonyl participation leading to a cyclized ion.