685-91-6

Basic information

• Product Name: Diethylacetamide
• Synonyms: n,n-diaethylacetamid;n,n-diethyl-acetamid;diethylacetamide;ACETIC ACID DIETHYLAMIDE;ACETYL DIETHYLAMINE;N-ACETYLDIETHYLAMINE;N,N-DIETHYLACETAMIDE;N,N-Diethylacetamide,99%
• CAS NO: 685-91-6
• Molecular Formula: C₆H₁₃NO
• Molecular Weight: 115.17
• EINECS: 211-685-2
• Mol File: 685-91-6.mol
• Article Data: 83

Chemical Properties

• Melting Point: <20 °C
• Boiling Point: 182-186 °C(lit.)
• Flash Point: 159 °F
• Appearance: clear colorless liquid
• Density: 0.925 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0291mmHg at 25°C
• Refractive Index: n20/D 1.440(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: 53.5g/l
• PKA: -0.41±0.70(Predicted)
• Water Solubility: Soluble in water.
• BRN: 1209428
• CAS DataBase Reference: Diethylacetamide(CAS DataBase Reference)
• NIST Chemistry Reference: Diethylacetamide(685-91-6)
• EPA Substance Registry System: Diethylacetamide(685-91-6)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-27-36/37/39-45
• WGK Germany: 3
• RTECS: AB7000000
• TSCA: Yes
• Hazardous Substances Data: 685-91-6(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless liquid

Uses

N,N-Diethylacetamide was used to investigate the spectroscopic properties ofN,N-diethyl-2-[(4-substituted)phenylsulfinyl] acetamides. It is commonly used as drug solvent.

Synthesis Reference(s)

Chemistry Letters, 18, p. 1983, 1989The Journal of Organic Chemistry, 59, p. 4035, 1994 DOI: 10.1021/jo00094a004

General Description

N,N-Diethylacetamide is commonly used as drug solvent.

Hazard

Toxic by ingestion.

Safety Profile

Moderately toxic by ingestion and intraperitoneal routes. Questionable carcinogen with experimental tumorigenic data. Flammable when exposed to heat or flame. To fight fire, use foam, mist, CO2, dry chemical. When heated to decomposition it emits toxic fumes of NOx.

Purification Methods

Dissolve the amide in cyclohexane, shake with anhydrous BaO and then filter. The procedure is repeated three times, and the cyclohexane is distilled off at atmospheric pressure. The crude amide is also fractionally distilled three times from anhydrous BaO. [Beilstein 4 III 349.]

InChI:InChI=1/C6H13NO/c1-3-5(4-2)6(7)8/h5H,3-4H2,1-2H3,(H2,7,8)

Synthetic route

ethyl 2,4-dinitrophenylacetoacetate (124089-63-0) + diethylamine (109-89-7) → diethylacetamide (685-91-6) + α-(2,4-dinitrophenyl)ethyl acetate (68084-17-3)

Conditions	Yield
In chloroform at 80℃; for 48h;	A 100% B n/a

acetic acid (64-19-7) + triethylamine (121-44-8) → diethylacetamide (685-91-6)

Conditions	Yield
With tetrachloromethane; potassium carbonate In dichloromethane for 9h; Inert atmosphere; Irradiation;	100%

vinyl acetate (108-05-4) + diethylamine (109-89-7) → diethylacetamide (685-91-6)

Conditions	Yield
With immobilization of Candida cylindracea lipase In hexane at 55℃; for 12h;	99%

ethanol (64-17-5) + ethylamine (75-04-7) + ethyl acetate (141-78-6) → diethylacetamide (685-91-6)

Conditions	Yield
With Cu 20%, Co 6%, Mn 4%, Mo 5%, Ag 0000.2%, alkaline earth metal 5%, rare earth metal 2% at 30 - 50℃; Temperature;	98.5%

acetic anhydride (108-24-7) + diethylamine (109-89-7) → diethylacetamide (685-91-6)

Conditions	Yield
With nickel dichloride at 20℃; for 0.166667h; Neat (no solvent);	97%
at 100℃; for 3h; Condensation;	91%
ZSM-35 zeolite In acetonitrile for 2h; Heating;	89.2%

diethylamine (109-89-7) + microgel-supported-CH3CO → diethylacetamide (685-91-6)

Conditions	Yield
In tetrahydrofuran at 25℃; for 13.5h; Inert atmosphere;	96.5%

diethylamine (109-89-7) + N-pivaloyl-N-methylacetamide → diethylacetamide (685-91-6)

Conditions	Yield
With aluminium trichloride In dichloromethane at 25℃; for 3.5h;	94%

ethyl acetate (141-78-6) + diethylamine (109-89-7) → diethylacetamide (685-91-6)

Conditions	Yield
With [Zn(BH4)2(py)] In tetrahydrofuran for 0.25h; Heating;	94%

trans-PdMe(I)(PMePh2)2 (42582-53-6) + carbon monoxide (201230-82-2) + diethylamine (109-89-7) → diethylacetamide (685-91-6) + N,N-diethyl-2-oxo-propanamide (22381-21-1)

Conditions	Yield
In tetrahydrofuran 10 atm CO pressure, magnetically stirred at room temp. for 1 day, totalyield: 95%;	A 7% B 93%
In tetrahydrofuran 1 atm CO pressure, magnetically stirred at room temp. for 1 day, total yield: 51%;	A 21% B 79%

N-methyl-acetamide (79-16-3) + diethylamine (109-89-7) → diethylacetamide (685-91-6)

Conditions	Yield
With aluminium trichloride In dichloromethane at 90℃; for 20h;	92%

S,S-diethyl-N-diethylamidodithiophosphite (42964-63-6) + acetic anhydride (108-24-7) → diethylacetamide (685-91-6) + O-acetyl S,S-diethyl phosphorodithioite (84103-76-4)

Conditions	Yield
for 20h; Product distribution; Ambient temperature;	A 91% B 88%

2-Chloro-N,N-diethylacetamide (2315-36-8) → diethylacetamide (685-91-6)

Conditions	Yield
With hydrogen In water at 120 - 140℃; under 22502.3 - 37503.8 Torr;	90%
With nickel In tetrahydrofuran at 20℃; for 2h;	90 % Spectr.
With potassium iodide; potassium carbonate In tetrahydrofuran
With hydrogen; triethylamine In methanol; water at 120℃; under 22502.3 Torr; for 95h; Autoclave;	90 %Chromat.

acetic acid butyl ester (123-86-4) + diethyl amine hydrochloride (660-68-4) → diethylacetamide (685-91-6)

Conditions	Yield
Stage #1: diethyl amine hydrochloride With diisobutylaluminium hydride In tetrahydrofuran; toluene Stage #2: acetic acid butyl ester In tetrahydrofuran at 20℃; for 2h;	90%

N-Hydroxymethyldiethylamine-acetate (2037-00-5) + bis(diethylamino)phenylphosphine (1636-14-2) → diethylacetamide (685-91-6) + diethylamidophenyl(N-diethylaminomethyl)phosphinate

Conditions	Yield
at 20℃; for 20h;	A 80% B 89.5%

diethylamine (109-89-7) + acetyl chloride (75-36-5) → diethylacetamide (685-91-6)

Conditions	Yield
With hydroxyapatite supported copper(I) oxide In acetonitrile at 50℃; for 0.25h;	89%
With iodine at 20℃; for 0.0166667h; Neat (no solvent);	86.3%
With pyridine In dichloromethane for 1h;	76%

trimethylsilyl diethylcarbamate (18279-61-3) + chloroacetyl chloride (79-04-9) → diethylacetamide (685-91-6)

Conditions	Yield
In dichloromethane for 0.25h; Ambient temperature;	89%

dipropyl diethylphosphoramidodithioite (53431-44-0) + acetic anhydride (108-24-7) → diethylacetamide (685-91-6) + O-acetyl S,S-dipropyl phosphorodithioite (84103-77-5)

Conditions	Yield
Product distribution; Ambient temperature;	A 88% B 82%

Trimethyl orthoacetate (1445-45-0) + diethyl amine hydrochloride (660-68-4) → diethylacetamide (685-91-6)

Conditions	Yield
for 4h; Reflux;	88%

O-acetyl-α-hydroxyisobutyric acid (15805-98-8) → diethylacetamide (685-91-6) + 2,3-dimethyl-2,3-butane diol (76-09-5) + Essigsaeure-2-hydroxy-1,1,2-trimethylpropylester (20127-81-5) + acetic anhydride (108-24-7)

Conditions	Yield
With triethylamine In acetonitrile Ambient temperature; electrolysis; Further byproducts given;	A 47% B 86.8% C 4.7% D n/a

O-acetyl-α-hydroxyisobutyric acid (15805-98-8) + triethylamine (121-44-8) → diethylacetamide (685-91-6) + 2,3-dimethyl-2,3-butane diol (76-09-5) + Essigsaeure-2-hydroxy-1,1,2-trimethylpropylester (20127-81-5) + acetic anhydride (108-24-7)

Conditions	Yield
In acetonitrile Ambient temperature; electrolysis; Further byproducts given;	A 47% B 86.8% C 4.7% D n/a

acetic anhydride (108-24-7) + triethylamine (121-44-8) → diethylacetamide (685-91-6)

Conditions	Yield
With tert.-butylhydroperoxide; water In acetonitrile at 70℃; for 1h;	85%

Acetic 4-methylthiobenzoic thioanhydride (64586-19-2) + Diethylamino-trimethyl-stannan (1068-74-2) → diethylacetamide (685-91-6) + 4,4'-Dimethyl-bis-thiobenzoyldisulfid (20710-51-4) + trimethyltin 4-methylbenzenecarbodithioate (42967-62-4)

Conditions	Yield
In hexane at 0℃; for 1h;	A 70% B 7% C 84%

Acetyl bromide (506-96-7) + S,S-diethyl-N-diethylamidodithiophosphite (42964-63-6) → diethylacetamide (685-91-6) + diethyl phosphorobromidodithioite (20472-60-0)

Conditions	Yield
Product distribution; -70 deg C to room temperature;	A 82% B 65%

Acetyl bromide (506-96-7) + dipropyl diethylphosphoramidodithioite (53431-44-0) → diethylacetamide (685-91-6) + dipropyl phosphorobromidodithioite

Conditions	Yield
Product distribution;	A 78% B 77%

5-ethoxycarbonyl-6-methyl-1,3-diacetyl-4-phenyl-3,4-dihydropyrimidin-2(1H)-one + diethylamine (109-89-7) → diethylacetamide (685-91-6)

Conditions	Yield
In tetrahydrofuran at 20℃;	78%

dipropyl diethylphosphoramidodithioite (53431-44-0) + acetic acid (64-19-7) → diethylacetamide (685-91-6) + tripropyl phosphorotrithioite (869-56-7) + O-acetyl S,S-dipropyl phosphorodithioite (84103-77-5)

Conditions	Yield
for 1h; Ambient temperature;	A 76% B n/a C n/a

acetic acid (64-19-7) + diethylamine (109-89-7) → diethylacetamide (685-91-6)

Conditions	Yield
tetraphosphorus decasulfide; triphenyl antimony oxide In benzene at 60℃; for 12h;	75%
With tetrachlorosilane; benzene

diethylamine (109-89-7) + thioacetic acid (507-09-5) → diethylacetamide (685-91-6)

Conditions	Yield
triphenyl antimony oxide In benzene at 20℃; for 8h;	75%

mixed anhydride of O,O-diisobutyl hydrogen phosphorothioate and tetraethylphosphorodiamidous acid (34469-24-4) + acetyl chloride (75-36-5) → diethylacetamide (685-91-6) + diethylphosphoramidous dichloride (1069-08-5) + bis(diisobutoxyphosphinothioyl)diethylphosphoramidite

Conditions	Yield
at 48 - 52℃; for 0.5h;	A 65% B 68% C 75%

dipropyl diethylphosphoramidodithioite (53431-44-0) + acetyl chloride (75-36-5) → diethylacetamide (685-91-6) + dipropyl phosphorochloridodithioite (4104-04-5)

Conditions	Yield
Product distribution;	A 73% B 69%

diethylacetamide (685-91-6) + 4-bromobenzenecarbonitrile (623-00-7) → 2-(4-cyanophenyl)-N,N-diethylacetamide

Conditions	Yield
Stage #1: diethylacetamide 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;	98%

diethylacetamide (685-91-6) + benzyl alcohol (100-51-6) → N,N-diethyl-3-phenylpropanamide (18859-19-3)

Conditions	Yield
With tri-tert-butyl phosphine; potassium tert-butylate; nickel diacetate In 1,4-dioxane; toluene at 80℃; for 12h; Inert atmosphere; Glovebox; Schlenk technique;	98%
With C19H26ClIrNOP; potassium tert-butylate In toluene at 80℃; for 12h; Schlenk technique; Inert atmosphere; Sealed tube; Green chemistry;	84%
With C29H55IrN3P2(1+)*Cl(1-); potassium tert-butylate In toluene at 120℃; for 15h; Schlenk technique; Inert atmosphere; Glovebox;	78%
With C22H34Cl2CoF3N5P2; potassium tert-butylate In tetrahydrofuran at 100℃; for 24h; Inert atmosphere; Sealed tube; Glovebox;	76%
With C23H21MnN2O3P(1+)*Br(1-); potassium tert-butylate In 1,4-dioxane at 130℃; for 15h; Schlenk technique; Inert atmosphere; Green chemistry;	56%

diethylacetamide (685-91-6) + 4-methoxycarbonylphenyl bromide (619-42-1) → methyl 4-((diethylcarbamoyl)methyl)benzoate

Conditions	Yield
Stage #1: diethylacetamide 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-methoxycarbonylphenyl 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;	97%

diethylacetamide (685-91-6) + 2,4,6-trimethylphenyl bromide (576-83-0) → N,N-diethyl-2-mesitylacetamide

Conditions	Yield
Stage #1: diethylacetamide 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: 2,4,6-trimethylphenyl 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;	96%

diethylacetamide (685-91-6) + 1-bromo-4-methoxy-benzene (104-92-7) → N,N-diethyl-2-(4-methoxyphenyl)acetamide (115348-15-7)

Conditions	Yield
With N-(dicyclohexylphosphino)-2-(2'-methylphenyl)-1H-indole; palladium diacetate; lithium tert-butoxide In toluene at 110℃; Inert atmosphere; Sealed tube; Microwave irradiation; chemoselective reaction;	95%
Stage #1: diethylacetamide 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;	93%

diethylacetamide (685-91-6) + 2-Bromo-6-methoxynaphthalene (5111-65-9) → N,N-diethyl-2-(2-methoxynaphthalen-6-yl)acetamide

Conditions	Yield
Stage #1: diethylacetamide 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;	95%

diethylacetamide (685-91-6) + sodium trisulfide + chloroacetone (78-95-5) → 2-acetyl benzo[b]thiophene (22720-75-8)

Conditions	Yield
In diethyl ether; water	95%

diethylacetamide (685-91-6) + 1-bromo-4-tert-butylbenzene (3972-65-4) → 2,2-bis(4-(tert-butyl)phenyl)-N,N-diethylacetamide (1449216-31-2)

Conditions	Yield
With N-(dicyclohexylphosphino)-2-(2'-methylphenyl)-1H-indole; palladium diacetate; sodium hexamethyldisilazane In toluene at 110℃; Inert atmosphere; Sealed tube; Microwave irradiation; chemoselective reaction;	95%

diethylacetamide (685-91-6) + 1-bromo-4-tert-butylbenzene (3972-65-4) → 2-(4-(tert-butyl)phenyl)-N,N-diethylacetamide

Conditions	Yield
With N-(dicyclohexylphosphino)-2-(2'-methylphenyl)-1H-indole; palladium diacetate; lithium tert-butoxide In toluene at 110℃; Inert atmosphere; Sealed tube; Microwave irradiation; chemoselective reaction;	94%
Stage #1: diethylacetamide 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-tert-butylbenzene With monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran; cyclohexane at 20℃; for 24h;	93%
Stage #1: diethylacetamide With bis(2,2,6,6-tetramethyl-1-piperidyl)zinc In toluene at 20℃; for 2h; Stage #2: 1-bromo-4-tert-butylbenzene With tri-tert-butyl phosphine; tris(dibenzylideneacetone)dipalladium (0) In toluene at 20℃; for 24h; Negishi coupling;	81 % Spectr.

bromochlorobenzene (106-39-8) + diethylacetamide (685-91-6) → 2-(4-chlorophenyl)-N,N-diethylacetamide (5292-72-8)

Conditions	Yield
Stage #1: diethylacetamide 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;	94%
With N-(dicyclohexylphosphino)-2-(2'-methylphenyl)-1H-indole; palladium diacetate; lithium tert-butoxide In toluene at 110℃; Inert atmosphere; Sealed tube; Microwave irradiation; chemoselective reaction;	87%

diethylacetamide (685-91-6) + bromobenzene (108-86-1) → N,N-diethyl-2,2-diphenylacetamide (3004-58-8)

Conditions	Yield
With N-(dicyclohexylphosphino)-2-(2'-methylphenyl)-1H-indole; palladium diacetate; sodium hexamethyldisilazane In toluene at 110℃; Inert atmosphere; Sealed tube; Microwave irradiation; chemoselective reaction;	94%

diethylacetamide (685-91-6) + meta-bromotoluene (591-17-3) → N,N-diethyl-2,2-di-m-tolylacetamide (1449216-33-4)

Conditions	Yield
With N-(dicyclohexylphosphino)-2-(2'-methylphenyl)-1H-indole; palladium diacetate; sodium hexamethyldisilazane In toluene at 110℃; Inert atmosphere; Sealed tube; Microwave irradiation; chemoselective reaction;	94%

diethylacetamide (685-91-6) + p-formylacetophenone (3457-45-2) → 3-(4-acetylphenyl)-N,N-diethyl-3-hydroxypropionamide

Conditions	Yield
Stage #1: diethylacetamide With bis(2,2,6,6-tetramethyl-1-piperidyl)zinc In toluene at 20℃; for 2h; Stage #2: p-formylacetophenone In toluene at 20℃; for 4h; aldol reaction;	93%

diethylacetamide (685-91-6) + diphenylzinc (1078-58-6) → (Zn(C6H5)(CH2C(O)N(CH2CH3)2))2

Conditions	Yield
With morpholine In toluene byproducts: C6H6; mixt. of N,N-diethylamide, morpholine (1 equiv) and ZnPh2 (3.0 equiv) intoluene heated to 50°C for 24 h;	93%
With morpholine In toluene byproducts: C6H6; mixt. of N,N-diethylamide, morpholine (1 equiv) and ZnPh2 (2.0 equiv) intoluene heated to 50°C for 24 h;	91%
With piperidine In toluene byproducts: C6H6; mixt. of N,N-diethylamide, piperidine and ZnPh2 in toluene heated to 50°C for 24 h;	90%

diethylacetamide (685-91-6) + 2-ethylsulfanyl-benzoic acid methyl ester (3795-78-6) → N,N-diethyl-3-(2-ethylsulfanylphenyl)-3-oxopropanamide (1353047-13-8)

Conditions	Yield
With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere;	93%

diethylacetamide (685-91-6) + 2-methylphenyl bromide (95-46-5) → N,N-diethyl-2-(2-methylphenyl)acetamide (40089-15-4)

Conditions	Yield
With N-(dicyclohexylphosphino)-2-(2'-methylphenyl)-1H-indole; palladium diacetate; lithium tert-butoxide In toluene at 110℃; Inert atmosphere; Sealed tube; Microwave irradiation; chemoselective reaction;	93%

o-fluorobromobenzene (1072-85-1) + diethylacetamide (685-91-6) → N,N-diethyl-2-(2-fluorophenyl)acetamide

Conditions	Yield
Stage #1: diethylacetamide 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;	92%

diethylacetamide (685-91-6) + (4-bromophenyl)(phenyl)methanone (90-90-4) → 2-(4-benzoylphenyl)-N,N-diethylacetamide

Conditions	Yield
Stage #1: diethylacetamide 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)(phenyl)methanone 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%

diethylacetamide (685-91-6) + para-bromoacetophenone (99-90-1) → 2-(4-acetylphenyl)-N,N-diethylacetamide

Conditions	Yield
Stage #1: diethylacetamide 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-bromoacetophenone 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%

diethylacetamide (685-91-6) + 1-Bromo-4-fluorobenzene (460-00-4) → N,N-diethyl-2-(4-fluorophenyl)acetamide (885900-99-2)

Conditions	Yield
With N-(dicyclohexylphosphino)-2-(2'-methylphenyl)-1H-indole; palladium diacetate; lithium tert-butoxide In toluene at 110℃; Inert atmosphere; Sealed tube; Microwave irradiation; chemoselective reaction;	92%

Upstream product

• 2622-07-3 hexaethylphosphorous triamide 
• 108-24-7 acetic anhydride 
• 64-19-7 acetic acid 
• 109-89-7 diethylamine 
• 127-09-3 sodium acetate 
• 88-10-8 N,N-diethylcarbamyl chloride 
• 108-05-4 vinyl acetate 
• 60-29-7 diethyl ether 
• 55847-36-4 2-chloroethane thioacetate 
• 110-22-5 diacetyl peroxide 
• 75-36-5 acetyl chloride 
• 75-05-8 acetonitrile 
• 64-17-5 ethanol 
• 10199-64-1 1-acetyl-1H-pyrazole 

Downstream Products

• 5450-73-7 (1-hydroxy-cyclohexyl)-acetic acid diethylamide 
• 1696-17-9 N,N-diethylbenzamide 
• 75-36-5 acetyl chloride 
• 5408-63-9 3-hydroxy-3-phenyl-butyric acid diethylamide 
• 5408-58-2 β-hydroxy-isovaleric acid diethylamide 
• 464-72-2 tetraphenylethane-1,2-diol 
• 129076-78-4 N-ethyl-N-(2-hydroxy-1-methyl-2,2-diphenylethyl)acetamide 
• 2524-37-0 ethyl orselinate 
• 105576-03-2 (E)-5-Iodo-4-phenyl-5-trimethylsilanyl-pent-4-enoic acid diethylamide 
• 121290-12-8 (E)-4-Diethylamino-4-p-tolyl-3-trifluoromethanesulfonyl-but-3-en-2-one 
• 1563-83-3 N-ethyl-diacetamide 
• 64-19-7 acetic acid 
• 625-50-3 N-ethylacetamide 
• 118282-59-0 2-(4-tert-Butyl-1-hydroxy-cyclohexyl)-N,N-diethyl-acetamide 

Relevant articles and documents

One-Pot Synthesis of Tertiary Amides from Organic Trichlorides through Oxygen Atom Incorporation from Air by Convergent Paired Electrolysis

A convergent paired electrolysis catalyzed by a B12 complex for the one-pot synthesis of a tertiary amide from organic trichlorides (R-CCl3) has been developed. Various readily available organic trichlorides, such as benzotrichloride and its derivatives, chloroform, dichlorodiphenyltrichloroethane (DDT), trichloro-2,2,2-trifluoroethane (CFC-113a), and trichloroacetonitrile (CNCCl3), were converted to amides in the presence of tertiary amines through oxygen incorporation from air at room temperature. The amide formation mechanism in the paired electrolysis, which was mediated by a cobalt complex, was proposed.

Production method of N,N-diethyl acetamide

The invention discloses a preparation method of N,N-dimethylformamide. The production method comprises the following steps: n a self-reflux reactor filled with a heterogeneous catalyst, firstly addingethyl acetate and ethylamine, carrying out heating to 30 DEG C within 10-20 minutes, then gradually adding ethanol within 20-30 minutes, then carrying out heating to 50-60 DEG C at a speed of 30-50 DEG C/h, performing reacting for 20-30 minutes, ending the reaction, and finally carrying out purifying to obtain N,N-diethyl acetamide. The obtained N,N-diethyl acetamide is high in yield, selectivityand purity, and the method is mild in reaction condition and easy to operate.

Amide Bond Formation Catalyzed by Recyclable Copper Nanoparticles Supported on Zeolite Y under Mild Conditions

A series of catalysts based on supported copper nanoparticles have been prepared and tested in the amide bond formation from tertiary amines and acid anhydrides, in the presence of tert-butyl hydroperoxide as an oxidant. Copper nanoparticles on zeolite Y (CuNPs/ZY) was found to be the most efficient catalyst for the synthesis of amides, working in acetonitrile as solvent, under ligand- and base-free conditions in air. The products were obtained in good to excellent yields and in short reaction times. The CuNPs/ZY system also exhibited higher catalytic activity than some commercially available copper and iron sources and it was reused in ten reaction cycles without any further pre-treatment. This methodology has been successfully scaled-up to a gram scale with no detriment to the yield.