1114-51-8

Basic information

• Product Name: N,N-Diethylpropionamide
• Synonyms: Propionamide, N,N-diethyl-;N,N-DIETHYLPROPIONAMIDE;N,N-Diethylpropionamide;N,N-Diethylpropiomide;Diethylamide of propionic acid;diethylamideofpropionicacid;Diethylpropionamide;n,n-diethyl-propanamid
• CAS NO: 1114-51-8
• Molecular Formula: C₇H₁₅NO
• Molecular Weight: 129.2
• Product Categories: Amides;Carbonyl Compounds;Organic Building Blocks
• Mol File: 1114-51-8.mol
• Article Data: 18

Chemical Properties

• Boiling Point: 77 °C12 mm Hg(lit.)
• Flash Point: 163 °F
• Appearance: /
• Density: 0.897 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.444mmHg at 25°C
• Refractive Index: n20/D 1.442(lit.)
• PKA: -0.41±0.70(Predicted)
• CAS DataBase Reference: N,N-Diethylpropionamide(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-Diethylpropionamide(1114-51-8)
• EPA Substance Registry System: N,N-Diethylpropionamide(1114-51-8)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36
• WGK Germany: 3
• RTECS: UE3567500
• Hazardous Substances Data: 1114-51-8(Hazardous Substances Data)

Usage

General Description

Gas phase ion/molecule reaction between dialkoxyborinium cation and N,N-diethylpropionamide was studied.

InChI:InChI=1/C7H15NO/c1-4-7(9)8(5-2)6-3/h4-6H2,1-3H3

Synthetic route

propionic acid (802294-64-0) + diethylamine (109-89-7) → N,N-diethylpropanamide (1114-51-8)

Conditions	Yield
Stage #1: propionic acid With niobium pentachloride In dichloromethane Stage #2: diethylamine In dichloromethane at 45 - 50℃; for 2.5h;	84%
With tetrachlorosilane; benzene
(i) 4-dimethylamino-but-3-yn-2-one, THF, (ii) /BRN= 605268/; Multistep reaction;

methyl(diethylamino)acetylene (4231-35-0) + N,N-dibenzylhydroxylamine (621-07-8) → N,N-diethylpropanamide (1114-51-8) + benzaldehyde (100-52-7) + benzylamine (100-46-9)

Conditions	Yield
In tetrahydrofuran for 0.5h; Ambient temperature;	A 80% B 10% C 7%

propionyl chloride (79-03-8) + N,N-diethyl-1,1,1-trimethylsilanamine (996-50-9) → N,N-diethylpropanamide (1114-51-8)

Conditions	Yield
In hexane for 5h; Ambient temperature;	71%

ethylmagnesium bromide (925-90-6) + C17H37NOP(1+)*Cl(1-) → N,N-diethylpropanamide (1114-51-8)

Conditions	Yield
With bis(triphenylphosphine)nickel(II) chloride In tetrahydrofuran at 20℃; for 2h;	58%

isocyanatoethene (3555-94-0) + methyl(diethylamino)acetylene (4231-35-0) → N,N-diethylpropanamide (1114-51-8) + 4-(diethylamino)-3-methyl-2-pyridinone (82639-26-7) + 2-(diethylamino)-3-methyl-4-pyridinone (82639-27-8) + N-(ethenylcarbamoyl)-4-(diethylamino)-3-methyl-2-pyridinone (82639-25-6)

Conditions	Yield
In diethyl ether Mechanism; Product distribution; Ambient temperature; vinyl isothiocyanate, var. mol. ratio of Educts;	A 15.5% B 15.5% C 42% D 28.5%
In diethyl ether 1.) reflux, 2.) room temp., overnight;	A 15.5% B 42% C 3.7% D 28.5%

propionyl chloride (79-03-8) + diethylamine (109-89-7) → N,N-diethylpropanamide (1114-51-8)

Conditions	Yield
With benzene

propionic acid anhydride (123-62-6) + diethylamine (109-89-7) → N,N-diethylpropanamide (1114-51-8)

ethyl N,N-diethylcarbamate (3553-80-8) + ethylmagnesium bromide (925-90-6) → N,N-diethylpropanamide (1114-51-8)

Conditions	Yield
In tetrahydrofuran

diethyl-amidosulfurous acid methyl ester (21954-69-8) + propionic acid (802294-64-0) → N,N-diethylpropanamide (1114-51-8)

Conditions	Yield
With pyridine

ethene (74-85-1) + carbon monoxide (201230-82-2) + diethylamine (109-89-7) → N,N-diethylpropanamide (1114-51-8)

Conditions	Yield
With cobalt(II) formate at 250 - 380℃;

1-(3,5-dimethyl-1H-pyrazol-1-yl)propan-1-one (37612-61-6) + diethylamine (109-89-7) → 3,5-dimethyl-1H-pyrazole (67-51-6) + N,N-diethylpropanamide (1114-51-8)

Conditions	Yield
In benzene at 29.5℃; Rate constant; other pyrazol, other amines;

1-diethylamino-1-(2-hydroxyethoxy)-1-propene (93702-88-6) → N,N-diethylpropanamide (1114-51-8)

Conditions	Yield
With sodium hydroxide at 80℃; for 2h;

1,1-dichloroethane (75-34-3) + carbon monoxide (201230-82-2) + diethylamine (109-89-7) → N,N-diethylpropanamide (1114-51-8) + N,N-diethyl-2-diethylaminopropionamide (106815-19-4)

Conditions	Yield
With triethylamine; dicobalt octacarbonyl at 100℃; under 38000 Torr; for 48h; Yield given. Yields of byproduct given;

1,1-Dibromoethane (557-91-5) + carbon monoxide (201230-82-2) + diethylamine (109-89-7) → N-formyldiethylamine (617-84-5) + N,N-diethylpropanamide (1114-51-8) + N,N,N',N'-tetraethylurea (1187-03-7) + N,N,N',N'-tetraethyloxamide (14288-05-2) + N,N-diethyl-2-diethylaminopropionamide (106815-19-4) + N,N,N',N'-tetraethyl-methylmalonamide (133746-51-7)

Conditions	Yield
With triethylamine; dicobalt octacarbonyl In hexane at 100℃; under 38000 Torr; for 48h; Product distribution; K2CO3, other solvents; other catalysts; other geminal dihaloalkanes;

...Expand

1,1-Dibromoethane (557-91-5) + carbon monoxide (201230-82-2) + diethylamine (109-89-7) → N,N-diethylpropanamide (1114-51-8) + N,N-diethyl-2-diethylaminopropionamide (106815-19-4) + N,N,N',N'-tetraethyl-methylmalonamide (133746-51-7)

Conditions	Yield
With triethylamine; dicobalt octacarbonyl In tetrahydrofuran at 100℃; under 38000 Torr; for 48h; K2CO3, other catalysts and solvents; Yield given. Yields of byproduct given;

triethylamine (121-44-8) + acrylic acid methyl ester (292638-85-8) → N,N-diethylpropanamide (1114-51-8)

Conditions	Yield
With ruthenium trichloride; triethylamine at 100℃; for 10h;

2-((E)-1-Diethylamino-propenyl)-1,1-dioxo-1,2-dihydro-1λ6-benzo[d]isothiazol-3-one (96439-62-2) → N,N-diethylpropanamide (1114-51-8) + saccharin (81-07-2)

Conditions	Yield
With water

methyl(diethylamino)acetylene (4231-35-0) + (cycloheptatrienylmethyl)carbene complex 1b → N,N-diethylpropanamide (1114-51-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 20.2 percent / H2SO4 / 4 h / 50 - 60 °C 2: 20percent aq. NaOH / 2 h / 80 °C View Scheme

1,4-dioxane (123-91-1) + ethene (74-85-1) + diethylamine (109-89-7) → N,N-diethylpropanamide (1114-51-8)

Conditions	Yield
In water

ethene (74-85-1) + diethylamine (109-89-7) + hexan-1-ol (111-27-3) → N,N-diethylpropanamide (1114-51-8)

Conditions	Yield
With CO

carbon monoxide (201230-82-2) + triethylamine (121-44-8) → diethylacetamide (685-91-6) + N-Ethyl,N-methylacetamide (38806-26-7) + N,N-diethylpropanamide (1114-51-8)

Conditions	Yield
With tertamethylammonium iodide; palladium dichloride In 1-methyl-pyrrolidin-2-one at 20 - 240℃; under 7500.75 - 48754.9 Torr; for 2.33333h; Autoclave;	A 43 %Chromat. B 12 %Chromat. C 37 %Chromat.

N,N-diethylpropanamide (1114-51-8) → 2-chloro-N,N-diethylpropionamide (54333-75-4)

Conditions	Yield
Stage #1: N,N-diethylpropanamide With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: With methyl chlorosulfate In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere;	100%

N,N-diethylpropanamide (1114-51-8) + 2-methylphenyl bromide (95-46-5) → N,N-diethyl-2-o-tolylpropanamide

Conditions	Yield
Stage #1: N,N-diethylpropanamide With sec.-butyllithium In tetrahydrofuran; cyclohexane at -78℃; for 1h; Stage #2: With zinc(II) chloride In tetrahydrofuran; cyclohexane at 20℃; for 0.166667h; Stage #3: 2-methylphenyl bromide With monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran; cyclohexane at 20℃; for 24h;	98%

4-bromo-phenol (106-41-2) + N,N-diethylpropanamide (1114-51-8) → N,N-diethyl-2-(4-hydroxyphenyl)propanamide

Conditions	Yield
Stage #1: N,N-diethylpropanamide With sec.-butyllithium In tetrahydrofuran; cyclohexane at -78℃; for 1h; Stage #2: With zinc(II) chloride In tetrahydrofuran; cyclohexane at 20℃; for 0.166667h; Stage #3: 4-bromo-phenol With {[P(t-Bu3)]PdBr}2; potassium hydride In tetrahydrofuran; cyclohexane at 20℃; for 24h;	95%

1-bromo-4-methoxy-benzene (104-92-7) + N,N-diethylpropanamide (1114-51-8) → N,N-diethyl-2-(4-methoxyphenyl)propanamide

Conditions	Yield
Stage #1: N,N-diethylpropanamide With sec.-butyllithium In tetrahydrofuran; cyclohexane at -78℃; for 1h; Stage #2: With zinc(II) chloride In tetrahydrofuran; cyclohexane at 20℃; for 0.166667h; Stage #3: 1-bromo-4-methoxy-benzene With monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran; cyclohexane at 20℃; for 24h;	94%

3-Bromothiophene (872-31-1) + N,N-diethylpropanamide (1114-51-8) → N,N-diethyl-2-(thiophen-3-yl)propionamide

Conditions	Yield
Stage #1: N,N-diethylpropanamide With sec.-butyllithium In tetrahydrofuran; cyclohexane at -78℃; for 1h; Stage #2: With zinc(II) chloride In tetrahydrofuran; cyclohexane at 20℃; for 0.166667h; Stage #3: 3-Bromothiophene With monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran; cyclohexane at 70℃; for 24h;	92%

2-bromoprop-1-ene (557-93-7) + N,N-diethylpropanamide (1114-51-8) → 2,3-dimethylbut-3-enoic acid diethylamide

Conditions	Yield
Stage #1: N,N-diethylpropanamide With sec.-butyllithium In tetrahydrofuran; cyclohexane at -78℃; for 1h; Stage #2: With zinc(II) chloride In tetrahydrofuran; cyclohexane at 20℃; for 0.166667h; Stage #3: 2-bromoprop-1-ene With monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran; cyclohexane at 20℃; for 24h;	92%

N,N-diethylpropanamide (1114-51-8) + 2-Bromo-6-methoxynaphthalene (5111-65-9) → N,N-diethyl-2-(2-methoxynaphthalen-6-yl)propanamide

Conditions	Yield
Stage #1: N,N-diethylpropanamide With sec.-butyllithium In tetrahydrofuran; cyclohexane at -78℃; for 1h; Stage #2: With zinc(II) chloride In tetrahydrofuran; cyclohexane at 20℃; for 0.166667h; Stage #3: 2-Bromo-6-methoxynaphthalene With monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran; cyclohexane at 20℃; for 24h;	92%

N,N-diethylpropanamide (1114-51-8) + (4-bromophenyl)thioanisole (104-95-0) → N,N-diethyl-2-(4-methylsulfanylphenyl)propionamide

Conditions	Yield
Stage #1: N,N-diethylpropanamide With sec.-butyllithium In tetrahydrofuran; cyclohexane at -78℃; for 1h; Stage #2: With zinc(II) chloride In tetrahydrofuran; cyclohexane at 20℃; for 0.166667h; Stage #3: (4-bromophenyl)thioanisole With monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran; cyclohexane at 20℃; for 24h;	91%

N,N-diethylpropanamide (1114-51-8) + 4-bromobenzenecarbonitrile (623-00-7) → 2-(4-cyanophenyl)-N,N-diethylpropanamide

Conditions	Yield
Stage #1: N,N-diethylpropanamide With sec.-butyllithium In tetrahydrofuran; cyclohexane at -78℃; for 1h; Stage #2: With zinc(II) chloride In tetrahydrofuran; cyclohexane at 20℃; for 0.166667h; Stage #3: 4-bromobenzenecarbonitrile With monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran; cyclohexane at 20℃; for 24h;	91%

N,N-diethylpropanamide (1114-51-8) + p-trifluoromethylphenyl bromide (402-43-7) → N,N-diethyl-2-(4-(trifluoromethyl)phenyl)propanamide

Conditions

Yield

Stage #1: N,N-diethylpropanamide With sec.-butyllithium In tetrahydrofuran; cyclohexane at -78℃; for 1h; Stage #2: With zinc(II) chloride In tetrahydrofuran; cyclohexane at 20℃; for 0.166667h; Stage #3: p-trifluoromethylphenyl bromide With monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran; cyclohexane at 20℃; for 24h;

90%

N,N-diethylpropanamide (1114-51-8) + 4-bromo-aniline (106-40-1) → 2-(4-aminophenyl)-N,N-diethylpropanamide

Conditions	Yield
Stage #1: N,N-diethylpropanamide With sec.-butyllithium In tetrahydrofuran; cyclohexane at -78℃; for 1h; Stage #2: With zinc(II) chloride In tetrahydrofuran; cyclohexane at 20℃; for 0.166667h; Stage #3: 4-bromo-aniline With {[P(t-Bu3)]PdBr}2; potassium hydride In tetrahydrofuran; cyclohexane at 20℃; for 24h;	90%

dimethyltitanocene (1271-66-5) + N,N-diethylpropanamide (1114-51-8) → 1-Bromo-2-butanone (816-40-0)

Conditions	Yield
Stage #1: dimethyltitanocene; N,N-diethylpropanamide In toluene at 65℃; Schlenk technique; Inert atmosphere; Stage #2: With bromine In toluene at -78℃; for 0.0333333h; Schlenk technique; Inert atmosphere; Stage #3: With water In toluene at 20℃; for 1h; Schlenk technique; Inert atmosphere; regioselective reaction;	90%

N,N-diethylpropanamide (1114-51-8) + 2-bromoanisole (578-57-4) → N,N-diethyl-2-(2-methoxyphenyl)propanamide

Conditions	Yield
Stage #1: N,N-diethylpropanamide With sec.-butyllithium In tetrahydrofuran; cyclohexane at -78℃; for 1h; Stage #2: With zinc(II) chloride In tetrahydrofuran; cyclohexane at 20℃; for 0.166667h; Stage #3: 2-bromoanisole With monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran; cyclohexane at 20℃; for 24h;	88%

bromochlorobenzene (106-39-8) + N,N-diethylpropanamide (1114-51-8) → 2-(4-chlorophenyl)-N,N-diethylpropanamide

Conditions	Yield
Stage #1: N,N-diethylpropanamide With sec.-butyllithium In tetrahydrofuran; cyclohexane at -78℃; for 1h; Stage #2: With zinc(II) chloride In tetrahydrofuran; cyclohexane at 20℃; for 0.166667h; Stage #3: bromochlorobenzene With monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran; cyclohexane at 20℃; for 24h;	87%

N,N-diethylpropanamide (1114-51-8) + para-nitrophenyl bromide (586-78-7) → N,N-diethyl-2-(4-nitrophenyl)propionamide

Conditions	Yield
Stage #1: N,N-diethylpropanamide With sec.-butyllithium In tetrahydrofuran; cyclohexane at -78℃; for 1h; Stage #2: With zinc(II) chloride In tetrahydrofuran; cyclohexane at 20℃; for 0.166667h; Stage #3: para-nitrophenyl bromide With monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran; cyclohexane at 20℃; for 24h;	87%

3-Bromopyridine (626-55-1) + N,N-diethylpropanamide (1114-51-8) → N,N-diethyl-2-(pyridin-3-yl)propanamide

Conditions	Yield
Stage #1: N,N-diethylpropanamide With sec.-butyllithium In tetrahydrofuran; cyclohexane at -78℃; for 1h; Stage #2: With zinc(II) chloride In tetrahydrofuran; cyclohexane at 20℃; for 0.166667h; Stage #3: 3-Bromopyridine With monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran; cyclohexane at 70℃; for 24h;	86%

o-fluorobromobenzene (1072-85-1) + N,N-diethylpropanamide (1114-51-8) → N,N-diethyl-2-(2-fluorophenyl)propanamide

Conditions	Yield
Stage #1: N,N-diethylpropanamide With sec.-butyllithium In tetrahydrofuran; cyclohexane at -78℃; for 1h; Stage #2: With zinc(II) chloride In tetrahydrofuran; cyclohexane at 20℃; for 0.166667h; Stage #3: o-fluorobromobenzene With monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran; cyclohexane at 20℃; for 24h;	86%

N,N-diethylpropanamide (1114-51-8) + uranium(IV) bromide (13470-20-7) → UBr4*3C2H5CON(C2H5)2

Conditions	Yield
In dichloromethane addn. of a large excess of ligand in CH2Cl2 to a suspn. of UBr4 in CH2Cl2; stirring for ca 1 h; evapn., dark green oil solidified with toluene; washed with toluene, n-pentane; dried in vac. for 10 h; elem. anal.;	84%

N,N-diethylpropanamide (1114-51-8) + 2,4-dimethoxy-N-(phenylmethylene)benzeneamine (80312-17-0) → C22H30N2O3

Conditions	Yield
With potassium hexamethylsilazane; bis[(3aR,8aS)-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-2-yl]methane In tetrahydrofuran at -78℃; for 24h; Mannich Aminomethylation; Inert atmosphere; stereoselective reaction;	81%

N,N-diethylpropanamide (1114-51-8) + thorium tetrabromide (13453-49-1) → {ThBr3(C2H5CON(C2H5)2)3}(1+)*Br(1-)={ThBr3(C2H5CON(C2H5)2)3}Br (98538-71-7)

Conditions	Yield
In tetrahydrofuran an excess of C2H5CON(C2H5)2 was added to a filtered soln. of ThBr4;; after 30 min the product was separated, washed twice with THF, and once with n-pentane, and dried for 8 h in vac.; elem.anal.;;	80%

N,N-diethylpropanamide (1114-51-8) + 5-Fluor-2-(4-fluorphenyl)-4-(trifluormethyl)oxazol (83081-29-2) → 2-<2-(4-Fluorphenyl)-4-(trifluormethyl)oxazol-5-yl>propansaeure-diethylamid (116672-11-8)

Conditions	Yield
In hexane Heating;	75%

thorium nitrate pentahydrate + N,N-diethylpropanamide (1114-51-8) → Th(4+)*4NO3(1-)*2.67H5C2CON(C2H5)2=Th(NO3)4*2.67C2H5CON(C2H5)2

Conditions	Yield
In ethanol addn. of large excess of the ligand (in abs. ethanol) to stirred soln. (abs. ethanol); stirring (1 h);; evapn. (colorless oil); dissolving (CH2Cl2); filtrate: evapn. to dryness; solidification overnight under pentane; washing (3 times/n-pentane); drying (vac./8 h); elem. anal.;;	72%

N,N-diethylpropanamide (1114-51-8) + methyloxirane (75-56-9, 16033-71-9) → 4-hydroxy-2-methyl-pentanoic acid diethylamide (338974-34-8)

Conditions	Yield
With lithium diisopropyl amide In tetrahydrofuran	71%

N,N-diethylpropanamide (1114-51-8) + propargyl bromide (106-96-7) → N,N-diethyl-2-methylpent-4-ynamide (1616976-79-4)

Conditions	Yield
With n-butyllithium; N-ethyl-N,N-diisopropylamine In tetrahydrofuran; hexane; toluene at -75 - 20℃; Inert atmosphere;	71%

N,N-diethylpropanamide (1114-51-8) + uranium(IV) chloride (10026-10-5) → {UCl3(N,N'-diethylpropionamide)4}{UCl5(N,N'-diethylpropionamide)} (82739-32-0)

Conditions	Yield
In tetrahydrofuran under N2, large excess of ligand added to soln. of UCl4 in THF, stirredfor 24 h; evapd. slowly in vac.; elem. anal.;	70%

zinc(II) nitrate hexahydrate + N,N-diethylpropanamide (1114-51-8) + benzene-1,3,5-tricarboxylic acid (554-95-0) → 11Zn(2+)*6C9H3O6(3-)*4NO3(1-)*8C7H15NO

Conditions	Yield
at 120℃; for 24h;	65%

N,N-diethylpropanamide (1114-51-8) → N,N-diethylpropylamine (4458-31-5)

Conditions	Yield
With hydrogen; hexarhodium hexadecacarbonyl; decacarbonyldirhenium(0) In 1,2-dimethoxyethane at 160℃; under 76000 Torr; for 36h;	62%
With dodecacarbonyl-triangulo-triruthenium; hydrogen; molybdenum hexacarbonyl In 1,2-dimethoxyethane at 160℃; under 75007.5 Torr; for 16h; Inert atmosphere;
With hydrogen In 1,2-dimethoxyethane at 160℃; under 22502.3 Torr; for 20h; Inert atmosphere; Autoclave; Molecular sieve;
With [(SIMes)PFMe2][B(C6F5)4]2; phenylsilane at 100℃; for 24h; Reagent/catalyst; Inert atmosphere; Schlenk technique; Glovebox;

Upstream product

• 123-62-6 propionic acid anhydride 
• 109-89-7 diethylamine 
• 75-34-3 1,1-dichloroethane 
• 201230-82-2 carbon monoxide 
• 557-91-5 1,1-Dibromoethane 
• 3555-94-0 isocyanatoethene 
• 4231-35-0 methyl(diethylamino)acetylene 
• 621-07-8 N,N-dibenzylhydroxylamine 
• 96439-62-2 2-((E)-1-Diethylamino-propenyl)-1,1-dioxo-1,2-dihydro-1λ⁶-benzo[d]isothiazol-3-one 
• 79-03-8 propionyl chloride 
• 430-71-7 propionyl fluoride 
• 121-44-8 triethylamine 
• 74-85-1 ethene 
• 111-27-3 hexan-1-ol 

Downstream Products

• 96-22-0 pentan-3-one 
• 116672-17-4 2-<2-(4-Chlorphenyl)-4-(trifluormethyl)thiazol-5-yl>propansaeure-diethylamid 
• 2445-82-1 3-methylcoumarine 
• 51975-15-6 N,N-Diethyl-2-methyl-3-oxo-3-phenylpropanamid 
• 106181-39-9 (2RS,3SR)-N,N-diethyl-3-hydroxy-2-methyl-3-phenylpropionamide 
• 116782-28-6 erythro-N,N-diethyl-3-hydroxy-2-methyl-3-phenylpropanamide 
• 4458-31-5 N,N-diethylpropylamine 
• 54333-75-4 2-chloro-N,N-diethylpropionamide 
• 105279-00-3 (R)-N,N-diethyl-2-methyl-3-(2-phenylquinolin-4-yl)propanamide 
• 105306-74-9 (S)-N,N-diethyl-2-methyl-3-(2-phenylquinolin-4-yl)propanamide 
• 1536470-50-4 C₄₂H₇₆Li₂N₆O₄ 
• 816-40-0 1-Bromo-2-butanone 
• 74-84-0 ethane 

Relevant articles and documents

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Carboxylic Acid Deoxyfluorination and One-Pot Amide Bond Formation Using Pentafluoropyridine (PFP)

This work describes the application of pentafluoropyridine (PFP), a cheap commercially available reagent, in the deoxyfluorination of carboxylic acids to acyl fluorides. The acyl fluorides can be formed from a range of acids under mild conditions. We also demonstrate that PFP can be utilized in a one-pot amide bond formation via in situ generation of acyl fluorides. This one-pot deoxyfluorination amide bond-forming reaction gives ready access to amides in yields of ≤94%.

PROCESS FOR PREPARING SECONDARY AMIDES BY CARBONYLATION OF A CORRESPONDING TERTIARY AMINE

The present invention relates to a process for preparing secondary amides with good selectivity by carbonylating a corresponding tertiary amine with carbon monoxide in a reaction mixture in the presence of a metal catalyst and in the presence of a halogen containing promoter. The metal catalyst comprises palladium. A same or even a much better catalytic activity can be obtained with palladium than with the much more expensive rhodium, especially when the palladium is used in a low concentration. Moreover, also a good selectivity can be achieved.

Niobium pentachloride promoted conversion of carboxylic acids to carboxamides: Synthesis of the 4-aryl-1,2,3,4-tetrahydroisoquinoline alkaloid structures

A practical method for the conversion of carboxylic acids to the corresponding carboxamides mediated by niobium pentachloride under mild conditions is described. The synthesis of the 4-aryl-1,2,3,4-tetrahydroisoquinoline alkaloid structures was accomplished via benzylic lithiation of N-methyl-3,4-dimethoxy-2-(4′-methoxybenzyl)benzamide.