5411-63-2

Basic information

• Product Name: 2-ButenaMide, N,N-diethyl-3-Methyl-
• Synonyms: 2-ButenaMide, N,N-diethyl-3-Methyl-;N,N-diethyl-3-methyl-2-Butenamide;N,N-diethyl-3-methylbut-2-enamide
• CAS NO: 5411-63-2
• Molecular Formula: C9H17NO
• Molecular Weight: 155.23738
• Mol File: 5411-63-2.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 259.3°Cat760mmHg
• Flash Point: 109°C
• Appearance: /
• Density: 0.887g/cm³
• Vapor Pressure: 0.0131mmHg at 25°C
• Refractive Index: 1.454
• CAS DataBase Reference: 2-ButenaMide, N,N-diethyl-3-Methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-ButenaMide, N,N-diethyl-3-Methyl-(5411-63-2)
• EPA Substance Registry System: 2-ButenaMide, N,N-diethyl-3-Methyl-(5411-63-2)

Safety Data

• Hazardous Substances Data: 5411-63-2(Hazardous Substances Data)

Usage

General Description

2-Butenamide, N,N-diethyl-3-methyl- is a chemical compound with the molecular formula C10H19NO. It is an amide derivative with a butenamide structure, and it contains two ethyl groups and a methyl group. 2-ButenaMide, N,N-diethyl-3-Methyl- is commonly used as a reactant in organic synthesis and pharmaceutical research due to its versatile reactivity and potential as a building block for the production of various compounds. It is also used in the development of agrochemicals and as a precursor in the synthesis of dyes and pigments. Additionally, it has been studied for its potential biological activity and medicinal properties.

InChI:InChI=1/C9H17NO/c1-5-10(6-2)9(11)7-8(3)4/h7H,5-6H2,1-4H3

Synthetic route

3,3-Dimethylacryloyl chloride (3350-78-5) + diethylamine (109-89-7) → N,N-dimethylamino-3,3-diethylacrylamide (5411-63-2)

Conditions	Yield
	90%
With diethyl ether

n-butyllithium (109-72-8, 29786-93-4) + N,N-diethyl-1,2,2-trichlorovinylamine (686-10-2) + acetone (67-64-1) → N,N-dimethylamino-3,3-diethylacrylamide (5411-63-2)

Conditions	Yield
(i), (ii) /BRN= 635680/, (iii) (hydrolysis); Multistep reaction;

2-methylallylmagnesium chloride (5674-01-1) + 2,2-Dimethyl-but-3-enoic acid diethylamide → N,N-dimethylamino-3,3-diethylacrylamide (5411-63-2) + N,N-diethyl-3-methyl-3-butenamide (62721-80-6)

Conditions	Yield
In tetrahydrofuran; hexane at 20℃; for 1h; Yield given. Yields of byproduct given;
With lithium diisopropyl amide In tetrahydrofuran; hexane at 20℃; for 1h; Yield given. Yields of byproduct given;

carbon monoxide (201230-82-2) + diethylamine (109-89-7) + 3-Chloro-2-methylpropene (563-47-3) → diethyl-methallyl-amine (19737-36-1) + N,N-dimethylamino-3,3-diethylacrylamide (5411-63-2) + N,N-diethyl-3-methyl-3-butenamide (62721-80-6) + 4-Methyl-2-oxo-pent-3-enoic acid diethylamide

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride In benzene under 76000 Torr; Ambient temperature;

N,N-dimethylamino-3,3-diethylacrylamide (5411-63-2) + bis(pinacol)diborane (73183-34-3) → N,N-diethyl-3-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)butanamide

Conditions	Yield
With methanol; water; caesium carbonate; bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine In toluene at 20℃; for 7h;	80%

triethylsilyl chloride (994-30-9) + N,N-dimethylamino-3,3-diethylacrylamide (5411-63-2) → (Z)-N,N-diethyl-3-methyl-4-triethylsilyl-but-2-enamide (1174909-04-6) + (E)-N,N-diethyl-3-methyl-4-triethylsilyl-but-2-enamide (1174909-05-7)

Conditions	Yield
Stage #1: N,N-dimethylamino-3,3-diethylacrylamide With lithium diisopropyl amide In tetrahydrofuran at -78 - -75℃; for 1h; Inert atmosphere; Stage #2: triethylsilyl chloride In tetrahydrofuran at -78℃; for 18.5h; Inert atmosphere; Reflux; Stage #3: With water; ammonium chloride In tetrahydrofuran Saturated solution; optical yield given as %de; diastereoselective reaction;	A 21% B 47%

N,N-dimethylamino-3,3-diethylacrylamide (5411-63-2) + 1-chloro-2,4-dimethoxybenzene (7051-13-0) → 5,7-dimethoxy-2-methyl-4-naphthol (106914-39-0)

Conditions	Yield
With lithium cyclohexylisopropylamide In tetrahydrofuran -78 deg C, 1 h, rt;	46%

chloro-trimethyl-silane (75-77-4) + N,N-dimethylamino-3,3-diethylacrylamide (5411-63-2) → (Z)-N,N-diethyl-3-methyl-4-trimethylsilyl-but-2-enamide (1174909-02-4) + (E)-N,N-diethyl-3-methyl-4-trimethylsilyl-but-2-enamide (1174909-03-5) + N,N-diethyl-3-methyl-3-butenamide (62721-80-6)

Conditions	Yield
Stage #1: N,N-dimethylamino-3,3-diethylacrylamide With lithium diisopropyl amide In tetrahydrofuran at -78 - -75℃; for 1h; Inert atmosphere; Stage #2: chloro-trimethyl-silane In tetrahydrofuran at -78℃; for 17.5h; Inert atmosphere; Reflux; Stage #3: With water; ammonium chloride In tetrahydrofuran Saturated solution; optical yield given as %de; diastereoselective reaction;	A 39% B 35% C n/a

3-methoxyphenyl bromide (2398-37-0) + N,N-dimethylamino-3,3-diethylacrylamide (5411-63-2) → 4-hydroxy-5-methoxy-2-methyl-naphthalene (22273-56-9)

Conditions	Yield
Stage #1: N,N-dimethylamino-3,3-diethylacrylamide With n-butyllithium; N-cyclohexylisopropylamine In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Stage #2: 3-methoxyphenyl bromide In tetrahydrofuran at 20℃; for 18h; Diels-Alder reaction; Inert atmosphere;	35%
With lithium cyclohexylisopropylamide 1) THF, hexane, -78 deg C, 1 h; 2) THF, -20 deg C, then room temp., overnight; Yield given. Multistep reaction;

3,3-Dimethylacryloyl chloride (3350-78-5) + diethylamine (109-89-7) → N,N-dimethylamino-3,3-diethylacrylamide (5411-63-2)

Conditions	Yield
	90%
With diethyl ether

n-butyllithium (109-72-8, 29786-93-4) + N,N-diethyl-1,2,2-trichlorovinylamine (686-10-2) + acetone (67-64-1) → N,N-dimethylamino-3,3-diethylacrylamide (5411-63-2)

Conditions	Yield
(i), (ii) /BRN= 635680/, (iii) (hydrolysis); Multistep reaction;

2-methylallylmagnesium chloride (5674-01-1) + 2,2-Dimethyl-but-3-enoic acid diethylamide → N,N-dimethylamino-3,3-diethylacrylamide (5411-63-2) + N,N-diethyl-3-methyl-3-butenamide (62721-80-6)

Conditions	Yield
In tetrahydrofuran; hexane at 20℃; for 1h; Yield given. Yields of byproduct given;
With lithium diisopropyl amide In tetrahydrofuran; hexane at 20℃; for 1h; Yield given. Yields of byproduct given;

carbon monoxide (201230-82-2) + diethylamine (109-89-7) + 3-Chloro-2-methylpropene (563-47-3) → diethyl-methallyl-amine (19737-36-1) + N,N-dimethylamino-3,3-diethylacrylamide (5411-63-2) + N,N-diethyl-3-methyl-3-butenamide (62721-80-6) + 4-Methyl-2-oxo-pent-3-enoic acid diethylamide

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride In benzene under 76000 Torr; Ambient temperature;

N,N-dimethylamino-3,3-diethylacrylamide (5411-63-2) + bis(pinacol)diborane (73183-34-3) → N,N-diethyl-3-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)butanamide

Conditions	Yield
With methanol; water; caesium carbonate; bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine In toluene at 20℃; for 7h;	80%

triethylsilyl chloride (994-30-9) + N,N-dimethylamino-3,3-diethylacrylamide (5411-63-2) → (Z)-N,N-diethyl-3-methyl-4-triethylsilyl-but-2-enamide (1174909-04-6) + (E)-N,N-diethyl-3-methyl-4-triethylsilyl-but-2-enamide (1174909-05-7)

Conditions	Yield
Stage #1: N,N-dimethylamino-3,3-diethylacrylamide With lithium diisopropyl amide In tetrahydrofuran at -78 - -75℃; for 1h; Inert atmosphere; Stage #2: triethylsilyl chloride In tetrahydrofuran at -78℃; for 18.5h; Inert atmosphere; Reflux; Stage #3: With water; ammonium chloride In tetrahydrofuran Saturated solution; optical yield given as %de; diastereoselective reaction;	A 21% B 47%

N,N-dimethylamino-3,3-diethylacrylamide (5411-63-2) + 1-chloro-2,4-dimethoxybenzene (7051-13-0) → 5,7-dimethoxy-2-methyl-4-naphthol (106914-39-0)

Conditions	Yield
With lithium cyclohexylisopropylamide In tetrahydrofuran -78 deg C, 1 h, rt;	46%

chloro-trimethyl-silane (75-77-4) + N,N-dimethylamino-3,3-diethylacrylamide (5411-63-2) → (Z)-N,N-diethyl-3-methyl-4-trimethylsilyl-but-2-enamide (1174909-02-4) + (E)-N,N-diethyl-3-methyl-4-trimethylsilyl-but-2-enamide (1174909-03-5) + N,N-diethyl-3-methyl-3-butenamide (62721-80-6)

Conditions	Yield
Stage #1: N,N-dimethylamino-3,3-diethylacrylamide With lithium diisopropyl amide In tetrahydrofuran at -78 - -75℃; for 1h; Inert atmosphere; Stage #2: chloro-trimethyl-silane In tetrahydrofuran at -78℃; for 17.5h; Inert atmosphere; Reflux; Stage #3: With water; ammonium chloride In tetrahydrofuran Saturated solution; optical yield given as %de; diastereoselective reaction;	A 39% B 35% C n/a

3-methoxyphenyl bromide (2398-37-0) + N,N-dimethylamino-3,3-diethylacrylamide (5411-63-2) → 4-hydroxy-5-methoxy-2-methyl-naphthalene (22273-56-9)

Conditions	Yield
Stage #1: N,N-dimethylamino-3,3-diethylacrylamide With n-butyllithium; N-cyclohexylisopropylamine In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Stage #2: 3-methoxyphenyl bromide In tetrahydrofuran at 20℃; for 18h; Diels-Alder reaction; Inert atmosphere;	35%
With lithium cyclohexylisopropylamide 1) THF, hexane, -78 deg C, 1 h; 2) THF, -20 deg C, then room temp., overnight; Yield given. Multistep reaction;

N,N-dimethylamino-3,3-diethylacrylamide (5411-63-2) + 4-Bromoveratrole (2859-78-1) → 5,6-dimethoxy-2-methyl-4-naphthol (106914-41-4)

Conditions	Yield
Stage #1: N,N-dimethylamino-3,3-diethylacrylamide With n-butyllithium; N-cyclohexylisopropylamine In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Stage #2: 4-Bromoveratrole In tetrahydrofuran at 20℃; for 18h; Diels-Alder reaction; Inert atmosphere;	31%
With lithium cyclohexylisopropylamide 1) THF, hexane, -78 deg C, 1 h; 2) THF, -20 deg C, then room temp., overnight; Yield given. Multistep reaction;

N,N-dimethylamino-3,3-diethylacrylamide (5411-63-2) + 2,4-dibromo-1-(methoxymethoxy)benzene (21571-52-8) → 5-bromo-8-(methoxymethoxy)-3-methyl-1-naphthalenol (160538-97-6) + 8-bromo-5-(methoxymethoxy)-3-methyl-1-naphthalenol + N,N-diethyl-2-[2-bromo-5-(methoxymethoxy)phenyl]-3-methyl-3-butenoic acid amide + N,N-diethyl-2-[5-bromo-2-(methoxymethoxy)phenyl]-3-methyl-3-butenoic acid amide

Conditions	Yield
Stage #1: N,N-dimethylamino-3,3-diethylacrylamide With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 2h; Metallation; Stage #2: 2,4-dibromo-1-(methoxymethoxy)benzene With lithium cyclohexylisopropylamide In tetrahydrofuran; hexane at 0℃; for 14h; Cycloaddition; Condensation; Further byproducts given;	A 31% B 7% C n/a D n/a

N,N-dimethylamino-3,3-diethylacrylamide (5411-63-2) + N-cyclohexylisopropylamine (1195-42-2) + 2,4-dibromo-1-(methoxymethoxy)benzene (21571-52-8) → α-naphthol (90-15-3)

Conditions	Yield
With n-butyllithium In tetrahydrofuran	29%

N,N-dimethylamino-3,3-diethylacrylamide (5411-63-2) + 2,4-dibromo-1-(methoxymethoxy)benzene (21571-52-8) → 5-bromo-8-(methoxymethoxy)-3-methyl-1-naphthalenol (160538-97-6)

Conditions	Yield
With lithium cyclohexylisopropylamide	21%
With lithium cyclohexylisopropylamide In tetrahydrofuran at -78 - 0℃; for 24h;	20%

N,N-dimethylamino-3,3-diethylacrylamide (5411-63-2) + 1-bromo-3,4,5-trimethoxybenzene (2675-79-8) → 5,6,7-trimethoxy-2-methyl-4-naphthol (6395-25-1)

Conditions	Yield
Stage #1: N,N-dimethylamino-3,3-diethylacrylamide With n-butyllithium; N-cyclohexylisopropylamine In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Stage #2: 1-bromo-3,4,5-trimethoxybenzene In tetrahydrofuran at 20℃; for 18h; Diels-Alder reaction; Inert atmosphere;	21%

N,N-dimethylamino-3,3-diethylacrylamide (5411-63-2) + 2,2'-dimethoxy-3,3',5,5'-tetrabromobiphenyl (855255-50-4) → 4,4'-dibromodiospyrol

Conditions	Yield
Stage #1: N,N-dimethylamino-3,3-diethylacrylamide With 2,2,6,6-tetramethylpiperidinyl-lithium In tetrahydrofuran at -78℃; for 1h; Stage #2: 3,3',5,5'-tetrabromo-2,2'-dimethoxybiphenyl In tetrahydrofuran at -78 - 20℃;	20%

N,N-dimethylamino-3,3-diethylacrylamide (5411-63-2) + Limettin (487-06-9) → 1,3-Dimethoxy-9-methyl-benzo[c]chromen-6-one

Conditions	Yield
With trichlorophosphate	13%

N,N-dimethylamino-3,3-diethylacrylamide (5411-63-2) → N,N-diethyl-3-methylbutanamide (533-32-4) + 2-isopropyl-3,3-dimethyl-glutaric acid bis-diethylamide

Conditions	Yield
With lithium aluminium tetrahydride; diethyl ether

N,N-dimethylamino-3,3-diethylacrylamide (5411-63-2) → N,N-Diethyl-2,3-dibrom-3-methyl-buttersaeureamid (91367-35-0)

Conditions	Yield
With bromine In tetrachloromethane

bromobenzene (108-86-1) + N,N-dimethylamino-3,3-diethylacrylamide (5411-63-2) → 3-methylnaphthalen-1-ol (13615-40-2)

Conditions	Yield
With lithium cyclohexylisopropylamide 1) THF, hexane, -78 deg C, 1 h; 2) THF, -20 deg C, then room temp., overnight; Yield given. Multistep reaction;

N,N-dimethylamino-3,3-diethylacrylamide (5411-63-2) + 2-bromoanisole (578-57-4) → 4-hydroxy-5-methoxy-2-methyl-naphthalene (22273-56-9) + N,N-diethyl-2-isopropenyl-2-(3'-methoxyphenyl)acetamide (106914-38-9)

Conditions	Yield
With lithium cyclohexylisopropylamide Product distribution; multistep reaction: 1) THF, hexane, -78 deg C, 1 h; 2) THF, -20 deg C, thenn room temp., overnight. Investigation of different reagents and compounds;
With lithium cyclohexylisopropylamide 1) THF, hexane, -78 deg C, 1 h; 2) THF, -20 deg C, then room temp., overnight; Yield given. Multistep reaction. Yields of byproduct given;
With lithium cyclohexylisopropylamide 1) THF, hexane, -78 deg C, 1 h; 2) THF, room temp., overnight; Yield given. Multistep reaction. Yields of byproduct given;

N,N-dimethylamino-3,3-diethylacrylamide (5411-63-2) + 9-bromophenanthrene (573-17-1) → 3-Methyl-triphenylen-1-ol (106914-42-5)

Conditions	Yield
With lithium cyclohexylisopropylamide 1) THF, hexane, -78 deg C, 1 h; 2) THF, -20 deg C, then room temp., overnight; Yield given. Multistep reaction;

N,N-dimethylamino-3,3-diethylacrylamide (5411-63-2) + 1-bromo-2-(methoxymethoxy)benzene (68314-54-5) → 8-methoxymethoxy-3-methyl-1-naphthalenol (106914-40-3)

Conditions	Yield
With lithium cyclohexylisopropylamide 1) THF, hexane, -78 deg C, 1 h; 2) THF, -20 deg C, then room temp., overnight; Yield given. Multistep reaction;

N,N-dimethylamino-3,3-diethylacrylamide (5411-63-2) + 2-chloro-1,4-dimethoxybenzene (2100-42-7) → 5,8-dimethoxy-3-methylnaphthalen-1-ol (50559-08-5)

Conditions	Yield
With lithium cyclohexylisopropylamide 1) THF, hexane, -78 deg C, 1 h; 2) THF, -20 deg C, then room temp., overnight; Yield given. Multistep reaction;

N,N-dimethylamino-3,3-diethylacrylamide (5411-63-2) + 1-chloro-3,5-dimethoxybenzene (7051-16-3) → 5,7-dimethoxy-2-methyl-4-naphthol (106914-39-0)

Conditions	Yield
With lithium cyclohexylisopropylamide 1) THF, hexane, -78 deg C, 1 h; 2) THF, -20 deg C, then room temp., overnight; Yield given. Multistep reaction;

N,N-dimethylamino-3,3-diethylacrylamide (5411-63-2) + 2-chloro-5-methylanisole (73909-16-7) → 1-Hydroxy-8-methoxy-3,6-dimethyl-naphthalin (778-99-4)

Conditions	Yield
With lithium cyclohexylisopropylamide 1) THF, hexane, -78 deg C, 1 h; 2) THF, -20 deg C, then room temp., overnight; Yield given. Multistep reaction;

N,N-dimethylamino-3,3-diethylacrylamide (5411-63-2) → 2-isopropyl-3,3-dimethyl-glutaric acid

Conditions	Yield
Multi-step reaction with 2 steps 1: lithium alanate; diethyl ether 2: aqueous hydrochloric acid View Scheme

N,N-dimethylamino-3,3-diethylacrylamide (5411-63-2) → N,N-Diethyl-2,3-di-S-acetyl-3-methyl-buttersaeureamid (92158-68-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: Br2 / CCl4 2: Py / benzene View Scheme

N,N-dimethylamino-3,3-diethylacrylamide (5411-63-2) → C9H16NO(1-)

Conditions	Yield
With lithium diisopropyl amide In tetrahydrofuran at -78 - -20℃; for 1.25h; Inert atmosphere;

Upstream product

• 3350-78-5 3,3-Dimethylacryloyl chloride 
• 109-89-7 diethylamine 
• 109-72-8 n-butyllithium 
• 686-10-2 N,N-diethyl-1,2,2-trichlorovinylamine 
• 67-64-1 acetone 
• 201230-82-2 carbon monoxide 
• 563-47-3 3-Chloro-2-methylpropene 
• 5674-01-1 2-methylallylmagnesium chloride 

Downstream Products

• 533-32-4 N,N-diethyl-3-methylbutanamide 
• 13615-40-2 3-methylnaphthalen-1-ol 
• 22273-56-9 4-hydroxy-5-methoxy-2-methyl-naphthalene 
• 106914-38-9 N,N-diethyl-2-isopropenyl-2-(3'-methoxyphenyl)acetamide 
• 160538-97-6 5-bromo-8-(methoxymethoxy)-3-methyl-1-naphthalenol 
• 90-15-3 α-naphthol 

Relevant articles and documents

Anti-tumoral activities of dioncoquinones B and C and related naphthoquinones gained from total synthesis or isolation from plants

Dioncoquinones belong to a family of natural naphthoquinone products of interest due to their promising anti-tumoral and anti-infective activities. In particular, dioncoquinones A (5) and B (6) have been shown to be highly active against Leishmania major and multiple myeloma cells without any significant toxicity toward normal blood cells. Their effective concentrations against multiple myeloma cell lines were similar to those of melphalan, a well known DNA-alkylating agent used in a standard therapy against B cell lymphoma and multiple myeloma. We report on the first total synthesis of the highly oxygenated anti-tumoral agent dioncoquinone B (6) and the isolation of its new, even higher-oxygenated analogs, dioncoquinones C (7), D (8), and E (9), from cell cultures of Triphyophyllum peltatum. In addition, several derivatives of these compounds were synthesized, including dioncoquinone C (7), and a small library of naphthoquinones was created. Furthermore, the first structure-activity relationship (SAR) study on this class of compounds was conducted, showing that each of the three hydroxy groups, at C-3, C-5, and C-6, is required for improved anti-tumoral activities and decreased cytotoxicities.

Palladium-Catalyzed Double and Single Carbonylation of Aryl Halides and Allylic Compounds

After a brief introduction summarizing the author's previous work concerning the double carbonylation of aryl halides catalyzed by palladium complexes, newly found catalytic processes (1) for converting allylic formates and chlorides into β,γ-unsaturated acids and (2) the double carbonylation of allylic chlorides to β,γ-unsaturated α-keto amides are described.Mechanisms which reasonably account for the catalytic processes are proposed on the basis of studies concerning the properties of the organopalladium complexes.

Reaction of lithiated senecioamide and related compounds with benzynes: Efficient syntheses of naphthols and naphthoquinones

-