5202-78-8

Usage

Uses

Used in Textile Industry:
N-Vinylacetamide 97 is used as a monomer for the synthesis of polymers that enhance the properties of textiles, such as improving their strength, durability, and resistance to environmental factors.
Used in Paper Industry:
N-Vinylacetamide 97 is used as a monomer in the production of polymers that are incorporated into paper products to improve their strength, water resistance, and overall quality.
Used in Water Treatment Industry:
N-Vinylacetamide 97 is used as a monomer to create polymers that are utilized in water treatment processes, such as flocculation, coagulation, and filtration, to improve water quality and remove contaminants.

InChI:InChI=1/C4H7NO/c1-3-5-4(2)6/h3H,1H2,2H3,(H,5,6)

Synthetic route

2-acetylaminoethanol (142-26-7) → acetylaminoethylene (5202-78-8)

Conditions	Yield
With succinic acid anhydride at 40 - 75℃; for 15h; Time; Inert atmosphere;	82.2%

N-(1-methoxyethyl)acetamide (55204-51-8) → acetylaminoethylene (5202-78-8)

Conditions	Yield
at 550℃;	70%
at 440℃; under 100 Torr;

2-methyl-4-methyl-4H-oxazolin-5-one (69773-71-3) → acetylaminoethylene (5202-78-8)

Conditions	Yield
at 550℃; under 0.1 - 0.2 Torr;	32%

N-(2-chloro-ethyl)-acetamide (7355-58-0) → acetylaminoethylene (5202-78-8)

Conditions	Yield
With sodium hydroxide; hexane
With sodium hydroxide; hexane
With sodium hydroxide; hexane

1,1-bis-acetylamino-ethane (5335-91-1) → acetylaminoethylene (5202-78-8)

Conditions	Yield
at 220℃;

N-(1-cyanoethyl)acetamide (19861-71-3) → acetylaminoethylene (5202-78-8)

Conditions	Yield
at 450℃; under 13 Torr;

C18H17NO (58286-92-3) → acetylaminoethylene (5202-78-8) + anthracene (120-12-7)

Conditions	Yield
In diphenylether at 250℃; Rate constant;

acetamide (60-35-5) + ethylidene diacetate (542-10-9) → 1,1-bis-acetylamino-ethane (5335-91-1) + N-acetylacetamide (625-77-4) + acetylaminoethylene (5202-78-8)

Conditions	Yield
With caesium carbonate In acetonitrile at 50℃; for 3h;	A 12.1 % Chromat. B 17.2 % Chromat. C 23.8 % Chromat.

acetamide (60-35-5) + ethylidene diacetate (542-10-9) → 1,1-bis-acetylamino-ethane (5335-91-1) + N-acetylacetamide (625-77-4) + acetylaminoethylene (5202-78-8) + N-(1-Acetylamino-ethyl)-N-vinyl-acetamide

Conditions	Yield
With caesium carbonate In acetonitrile at 50℃; for 3h; Product distribution; reactions in presence of further bases or Lewis acids;	A 12.1 % Chromat. B 17.2 % Chromat. C 23.8 % Chromat. D 1.6 % Chromat.

N-(α-isopropoxyethyl)acetamide → acetylaminoethylene (5202-78-8)

N-(1-methoxyethyl)acetamide (55204-51-8) → acetamide (60-35-5) + acetylaminoethylene (5202-78-8)

Conditions	Yield
at 330 - 350℃; Product distribution / selectivity;

Acetaldehyde oxime (107-29-9) + acetic anhydride (108-24-7) → acetylaminoethylene (5202-78-8)

Conditions	Yield
With copper(l) iodide; sodium hydrogensulfite In 1,2-dichloro-ethane at 120℃; for 12h; Inert atmosphere;

acetylaminoethylene (5202-78-8) + 4-Aminoacetophenone (99-92-3) → N-(6-acetyl-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl)acetamide

Conditions	Yield
With sodium dodecyl-sulfate In water at 20℃; for 1h; pH=1; Reagent/catalyst; Solvent; Temperature; Time; Green chemistry; diastereospecific reaction;	99%
With cerium(IV) sulphate In acetonitrile at 20℃; under 760.051 Torr; for 6h; Catalytic behavior; Temperature; diastereoselective reaction;	89%

acetylaminoethylene (5202-78-8) + 4.-brorno-thiophene-3-carboxylic acid ethyl ester (224449-33-6) → ethyl 4-(2-acetamidovinyl)thiophene-3-carboxylate

Conditions	Yield
With palladium diacetate; triethylamine; tris-(o-tolyl)phosphine In N,N-dimethyl-formamide at 80℃; for 12h; Inert atmosphere;	99%

acetylaminoethylene (5202-78-8) + 1-Bromo-3-phenylpropane (637-59-2) → N-ethenyl-N-(3-phenylpropyl)acetamide (1105508-27-7)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide Inert atmosphere;	98%

C6H4NCH2CHCCH2 (491-35-0) + acetylaminoethylene (5202-78-8) + Benzyl bromoacetate (5437-45-6) → benzyl (S)-4-acetamido-4-(4-methylquinolin-2-yl)butanoate

Conditions	Yield
With potassium phosphate; (R)-3,3'-bis(2,4,6-triisopropylphenyl)binol phosphoric acid; [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate; water In toluene at 25℃; for 15h; Schlenk technique; Inert atmosphere; Sealed tube; Irradiation; enantioselective reaction;	96%

acetylaminoethylene (5202-78-8) + p-methylbenzaldehyde oxime (3717-15-5) → (E)-4-methylbenzaldehyde O-1-(N-acetyl)aminoethyloxime (1140531-49-2)

Conditions	Yield
With 2,6-di-tert-butyl-pyridine; tris(4-bromophenyl)aminium hexachloroantimonate In dichloromethane at 20℃; for 0.166667h;	95%

acetylaminoethylene (5202-78-8) + Ac-FQPKCG-NH2 (1352790-18-1) → C36H56N10O9S (1352790-23-8)

Conditions	Yield
With GLUTATHIONE; 2,2’-azobis[2-(2-imidazolin-2-yl)propane] dihydrochloride for 1h; pH=4; Product distribution / selectivity; Acetate buffer; UV-irradiation;	95%
With GLUTATHIONE for 1h; pH=4; aq. acetate buffer; UV-irradiation;

acetylaminoethylene (5202-78-8) + Ethyl bromodifluoroacetate (667-27-6) + phenylboronic acid (98-80-6) → ethyl 4-acetamido-2,2-difluoro-4-phenylbutanoate

Conditions	Yield
With nickel(II) triflate; potassium carbonate; 5,5′-bis(trifluoromethyl)-2,2′-bipyridine In 1,4-dioxane at 80℃; for 8h; Inert atmosphere; Schlenk technique;	92%

p-toluene sulfinic acid (536-57-2) + acetylaminoethylene (5202-78-8) → N-[1-(p-toluenesulfonyl)ethyl]acetamide (1578252-28-4)

Conditions	Yield
With photoredox catalyst Ni/TiO2 In acetonitrile at 20℃; for 3.5h; Molecular sieve; Irradiation;	92%

6-methyl-4-tosyloxy-2(2H)-pyranone (31913-41-4) + acetylaminoethylene (5202-78-8) → N-(1-(6-methyl-2-oxo-2H-pyran-4-yl)vinyl)acetamide

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; N-ethyl-N,N-diisopropylamine; tris(dibenzylideneacetone)dipalladium (0) In 1,4-dioxane at 85℃; for 4h; Heck reaction;	91%

4-methyl-N-(2-methylallyl)-N-(3-phenylprop-2-yn-1-yl)benzenesulfonamide (869938-32-9) + acetylaminoethylene (5202-78-8) → (+)-N-[(5S*,7aR*)-7a-methyl-4-phenyl-2-tosyl-2,3,5,6,7,7a-hexahydro-1H-isoindol-5-yl]acetamide

Conditions	Yield
With bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; hydrogen; (R)-segphos In dichloromethane at 20℃; for 72h; Schlenk technique; stereoselective reaction;	91%

acetylaminoethylene (5202-78-8) + Ethyl bromodifluoroacetate (667-27-6) + 4-fluoroboronic acid (1765-93-1) → ethyl 2,2-difluoro-3-(4-fluorophenyl)-3-oxopropanoate (2262-04-6) + ethyl 4-acetamido-2,2-difluoro-5-(4-fluorophenyl)-5-oxopentanoate

Conditions	Yield
With carbon monoxide; water; C19H16ClFN2NiO3; potassium carbonate In 1,4-dioxane at 50℃; under 760.051 Torr; for 18h; Time; Schlenk technique; Sealed tube;	A 38 %Spectr. B 91%

9H-thioxanthen-9-ol (6783-74-0) + acetylaminoethylene (5202-78-8) → (9H-thioxanthen-9-yl)-acetaldehyde

Conditions	Yield
Stage #1: 9H-thioxanthen-9-ol; acetylaminoethylene With acetic acid at 20℃; for 1h; Stage #2: With hydrogenchloride for 1h;	90%

acetylaminoethylene (5202-78-8) → N-(1-methoxyethyl)acetamide (55204-51-8)

Conditions	Yield
With acetamide	90%
In methanol

acetylaminoethylene (5202-78-8) + histone H3 K27C → H3 Ks27Ac

Conditions	Yield
With GLUTATHIONE; 2,2’-azobis[2-(2-imidazolin-2-yl)propane] dihydrochloride for 2h; pH=4; Acetate buffer; UV-irradiation;	90%

acetylaminoethylene (5202-78-8) + histone H4 K16C → H4 Ks16Ac

Conditions	Yield
With dimethylsulfide; GLUTATHIONE; 2,2’-azobis[2-(2-imidazolin-2-yl)propane] dihydrochloride for 2h; pH=4; Product distribution / selectivity; Acetate buffer; UV-irradiation;	90%

acetylaminoethylene (5202-78-8) + thiophenol (108-98-5) → C10H13NOS

Conditions	Yield
With tris(bipyridine)ruthenium(II) dichloride hexahydrate In acetonitrile at 20℃; for 2h; Catalytic behavior; Solvent; Irradiation; regioselective reaction;	90%

acetylaminoethylene (5202-78-8) + phenylmethanethiol (100-53-8) → C11H15NOS

Conditions	Yield
With tris(bipyridine)ruthenium(II) dichloride hexahydrate In acetonitrile at 20℃; for 18h; Irradiation; regioselective reaction;	90%

acetylaminoethylene (5202-78-8) + 4-acetophenyl triflate (109613-00-5) → N-acetyl-1-(4'-acetylphenyl)ethenamine (823790-71-2)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; 1,1'-bis-(diphenylphosphino)ferrocene; tris(dibenzylideneacetone)dipalladium (0) In 1,4-dioxane at 85℃; for 1.75h; Heck coupling;	89%
With 1,3-bis-(diphenylphosphino)propane; triethylamine; palladium diacetate In N,N-dimethyl-formamide at 100℃; Heck reaction;	40%

acetylaminoethylene (5202-78-8) + Ethyl 4-bromobenzoate (5798-75-4) → ethyl 4-(1-acetamidovinyl)benzoate (1028431-82-4)

Conditions	Yield
With 1,3-bis-(diphenylphosphino)propane; triethylamine; palladium diacetate In isopropyl alcohol for 12h; Heck arylation; Heating;	89%

acetylaminoethylene (5202-78-8) + phenylmethanethiol (100-53-8) → 1-acetamido-2-benzylthioethane (60116-67-8)

Conditions	Yield
In water at 20℃; for 18h; Green chemistry; regioselective reaction;	88%
With 10-methyl-9-(2,4,6-trimethylphenyl) acridinium tetrafluoroborate In acetonitrile at 20℃; for 6h; Irradiation; Sealed tube;	82%
With 2,2’-azobis[2-(2-imidazolin-2-yl)propane] dihydrochloride at 20℃; for 0.5h; pH=4; Acetate buffer; UV-irradiation;

C6H4NCH2CHCCH2 (491-35-0) + acetylaminoethylene (5202-78-8) + bromoacetic acid methyl ester (96-32-2) → methyl (S)-4-acetamido-4-(4-methylquinolin-2-yl)butanoate

Conditions	Yield
With potassium phosphate; (R)-3,3'-bis(2,4,6-triisopropylphenyl)binol phosphoric acid; [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate; water In toluene at 25℃; for 15h; Reagent/catalyst; Schlenk technique; Inert atmosphere; Sealed tube; Irradiation; enantioselective reaction;	88%

Upstream product

• 7355-58-0 N-(2-chloro-ethyl)-acetamide 
• 142-26-7 2-acetylaminoethanol 
• 107-29-9 Acetaldehyde oxime 
• 108-24-7 acetic anhydride 
• 55204-51-8 N-(1-methoxyethyl)acetamide 
• 60-35-5 acetamide 
• 542-10-9 ethylidene diacetate 
• 69773-71-3 2-methyl-4-methyl-4H-oxazolin-5-one 
• 58286-92-3 C₁₈H₁₇NO 
• 19861-71-3 N-(1-cyanoethyl)acetamide 
• 5335-91-1 1,1-bis-acetylamino-ethane 

Downstream Products

• 73323-67-8 N-acetyl-α-aminopropionaldehyde 
• 73323-68-9 N-acetyl-3-aminopropanaldehyde 
• 1105508-27-7 N-ethenyl-N-(3-phenylpropyl)acetamide 
• 1105508-25-5 N-(4-methoxybenzyl)-N-vinylacetamide 
• 31053-31-3 2-acetyl-2H-isoquinolin-1-one 
• 491-30-5 1-isoquinolone 
• 823790-71-2 N-acetyl-1-(4'-acetylphenyl)ethenamine 
• 1028431-82-4 ethyl 4-(1-acetamidovinyl)benzoate 
• 823790-72-3 N-acetyl-1-(4'-cyanophenyl)ethenamine 
• 349537-57-1 methyl 3-(1-acetamidovinyl)benzoate 
• 177750-08-2 1-(4-methylphenyl)ethenylacetamide 
• 60-35-5 acetamide 
• 941-98-0 1'-naphthacetophenone 
• 65693-78-9 N-(1-(naphthalene-1-yl)vinyl)acetamide 

Relevant academic research and scientific papers

Access to multi-functionalized oxazolines via silver-catalyzed heteroannulation of enamides with sulfoxonium ylides

Disclosed herein is an efficient Ag-catalyzed [4 + 1] heteroannulation reaction of enamides with α-carbonyl sulfoxonium ylides. The diastereoselective transformation provides a practical access to a diverse range of multi-functionalized oxazoline derivatives. The synthetic utility of the resultant tetra-substituted oxazolines is further demonstrated by a series of useful manipulations into valuable building blocks of pharmaceutical relevance.

METHOD OF PRODUCING N-VINYLCARBOXYLIC ACID AMIDE

A method for producing an N-vinylcarboxylic acid amide is provided, the method focusing on unsaturated aldehydes that are contained as impurities generated during a reaction. The method for producing an N-vinylcarboxylic acid amide includes a step for controlling the contained amount of unsaturated aldehydes in the N-vinylcarboxylic acid amide to be not more than 20 mass ppm.

Preparation method of N-vinyl alkylamide

The invention relates to the technical field of vinyl compound production, in particular to a preparation method of Nvinyl alkyl amide. The preparation method comprises the following steps: A) under the action of a composite basic catalyst, reacting acetaldehyde with alkylamide to obtain Nhydroxyethyl alkylamide, and carrying out esterification reaction on the obtained Nhydroxyethyl alkylamide andacid anhydride to obtain an ester compound; wherein the composite basic catalyst comprises an inorganic base and an amine compound; and B) carrying out medium-temperature cracking on the ester compound, and carrying out vacuum distillation to obtain the Nvinyl alkylamide. Research finds that inorganic base and amine compounds are adopted as catalysts at the same time, so that the dosage of a basic catalyst required by reaction of Nhydroxyethyl alkylamide and anhydride can be remarkably reduced, the temperature required by subsequent cracking reaction is reduced, a reaction system tends to bemilder, and the reaction yield is improved. The yield and the purity of a reaction product can be remarkably improved while the energy consumption is reduced.

N-(1-HYDROXYETHYL)CARBOXAMIDE COMPOUND AND PROCESS FOR PRODUCING SAME

The present invention relates to an N-(1-hydroxyethyl)carboxamidecompound represented by formula(1) (in the formula, RA and RB represent independently from each other a hydrogen atom or an alkyl group having 1 to 4 carbon atoms except for a case where RA and RB represent a hydrogen atom at the same time) and a method for producing the same; a method for producing an N-(1-alkoxyethyl)carboxamide compound; a method for producing an N-vinyl carboxylic acid amide compound; and a method for producing an N-vinyl carboxylic acid amide (co)polymer. An N- (1-alkoxyethyl) carboxamide compound can be obtained by reacting N-(1-hydroxyethyl)carboxamide compound with alcohol in the presence of an acid catalyst, and an N-vinyl carboxylic acid amide compound, which is a monomer of the N-vinyl carboxylic acid amide (co)polymer, can be obtained by thermally decomposing or catalytically decomposing the N-(1-alkoxyethyl)carboxamide compound.

PROCESS FOR PRODUCING HIGH-PURITY N-VINYLCARBOXAMIDES

Disclosed is a process for producing high-purity N-vinylcarboxamides comprising: (A) a step of dissolving a crude N-vinylcarboxamide in an alcohol having 1 to 3 carbon atoms, the crude N-vinylcarboxamide containing 50 to 97% by mass of an N-vinylcarboxamide; (B) a step of adding an aliphatic hydrocarbon having 5 to 10 carbon atoms to the composition obtained in the step (A) to precipitate a crystal of the N-vinylcarboxamide; and (C) a step of separating the crystal of the N-vinylcarboxamide precipitated in the step (B).

HIGHLY POLYMERIZABLE N-VINYLCARBOXYLIC ACID AMIDE AND PRODUCTION PROCESS THEREOF

A highly polymerizable N-vinylcarboxylic acid amide having an N-1,3-butadienylcarboxylic acid amide content of 30 ppm or less, a process for producing the same, and a process for producing a homopolymer of N-vinylcarboxylic acid amide or a copolymer thereof with another copolymerizable monomer using the same. Also, a highly polymerizable N-vinyl carboxylic acid amide is produced by thermal cracking or catalytic cracking of N-(1-alkoxyethyl)carboxylic acid amide or ethylidenebiscarboxylic acid amide, wherein the N-vinylcarboxylic acid amide content of the N-(1-alkoxyethyl)carboxylic acid amide or ethylenebiscarboxylic acid amide is 10 wt % or less.

Highly polymerizable N-vinylcarboxylic acid amide and production process thereof

A highly polymerizable N-vinylcarboxylic acid amide having an N-1,3-butadienylcarboxylic acid amide content of 30 ppm or less, a process for producing the same, and a process for producing a homopolymer of N-vinylcarboxylic acid amide or a copolymer thereof with another copolymerizable monomer using the same. Also, a highly polymerizable N-vinyl carboxylic acid amide is produced by thermal cracking or catalytic cracking of N-(1-alkoxyethyl)carboxylic acid amide or ethylidenebiscarboxylic acid amide, wherein the N-vinylcarboxylic acid amide content of the N-(1-alkoxyethyl)carboxylic acid amide or ethylenebiscarboxylic acid amide is 10 wt % or less.

Reactions of ethylidene diacetate: Formation of N-vinylamide precursors ethylidene bisacetamide and ethylidene bisformamide

Ethylidene diacetate (EDA) reacts with formamide or acetamide under stoichiometric base or catalytic Lewis acid conditions to afford the corresponding ethylidene bisamides and N-vinylamides. Sn(OAc)2 afforded an overall 82.6% selectivity to the desired acetamide derivatives. Sn(OAc)2 and Zn(OAc)2 facilitate amide attack at the tertiary carbon of EDA.

Process for production of N-vinyl compound

The present invention provides a process for producing an N-vinyl compound, which comprises subjecting an N-(-alkoxyalkyl) compound to gas phase intramolecular alcohol elimination to convert said compound to an N-vinyl compound directly in one step, wherein a solid oxide containing phosphorus and an alkali metal and/or an alkaline earth metal is used as a catalyst. This process need not use any solvent or any auxiliary raw material and consequently can produce an N-vinyl compound simply and safely without generating any waste material derived from the auxiliary raw material.

A New Polymer Electrolyte Composed of Poly(N-vinylacetamide), Poly(ethylene glycol), and Lithium Trifluoromethanesulfonate

A new solid composite of poly(N-vinylacetamide), lithium trifluoromethanesulfonate, and poly(ethylene glycol) was prepared and characterized as a polymer electrolyte with high conductivity.