623-76-7

Basic information

• Product Name: 1,3-Diethylurea
• Synonyms: 1,3-diethyl-ure;sym-N,N'-Diethylurea;Urea, 1,3-diethyl-;urea,n,n’-diethyl;Urea,N,N’-diethyl-;N,N'-DIETHYLUREA;SYM-DIETHYLUREA;LABOTEST-BB LT01690259
• CAS NO: 623-76-7
• Molecular Formula: C₅H₁₂N₂O
• Molecular Weight: 116.16
• EINECS: 210-811-3
• Product Categories: Ureas;Carbonyl Compounds;Organic Building Blocks
• Mol File: 623-76-7.mol

Chemical Properties

• Melting Point: 112-113 °C(lit.)
• Boiling Point: 217.23°C (rough estimate)
• Flash Point: 121.1 °C
• Appearance: /
• Density: 1.0415
• Vapor Pressure: 0.0106mmHg at 25°C
• Refractive Index: 1.4616 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 16.53±0.46(Predicted)
• Water Solubility: Soluble in water.
• BRN: 1744741
• CAS DataBase Reference: 1,3-Diethylurea(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Diethylurea(623-76-7)
• EPA Substance Registry System: 1,3-Diethylurea(623-76-7)

Safety Data

• Hazard Codes: F,T
• Statements: 11-23/24/25-36/37/38
• Safety Statements: 22-24/25-36/37/39-15-3/7/9
• WGK Germany: 3
• RTECS: YS9354000
• Hazardous Substances Data: 623-76-7(Hazardous Substances Data)

Usage

Uses

1. Used in Pharmaceutical Industry:
1,3-Diethylurea is used as an intermediate in the synthesis of various pharmaceutical chemicals. Its ability to form a wide range of derivatives makes it a versatile building block for the development of new drugs and medications.
2. Used in Caffeine and Theophylline Production:
1,3-Diethylurea is utilized in the production of caffeine and theophylline, which are both central nervous system stimulants and widely used in the treatment of asthma and other respiratory conditions. 1,3-Diethylurea serves as a key precursor in the chemical synthesis process, enabling the efficient and cost-effective production of these important active pharmaceutical ingredients.
3. Used in Textile Industry:
In the textile industry, 1,3-Diethylurea is employed as a textile aid, where it is used to improve the properties of fabrics and fibers. Its application in this industry is attributed to its ability to enhance the softness, strength, and durability of textile materials, making it an essential component in the production of various textile products.
4. Used in Chemical Synthesis:
1,3-Diethylurea is also used as a reagent in various chemical synthesis processes, where it can be employed to produce a range of different compounds with diverse applications. Its unique chemical structure allows it to participate in a variety of reactions, making it a valuable tool in the synthesis of new and innovative materials.

InChI:InChI=1/C5H12N2O/c1-3-6-5(8)7-4-2/h3-4H2,1-2H3,(H2,6,7,8)

Synthetic route

ethylamine (75-04-7) + S-methyl N-ethylthiocarbamate (39076-43-2) → methylthiol (74-93-1) + N,N'-diethylurea (623-76-7)

Conditions	Yield
In water at 40℃; for 8h;	A n/a B 100%

ethyl isocyanate (109-90-0) → N,N'-diethylurea (623-76-7)

Conditions	Yield
With water; triethylamine In 1,4-dioxane at 20℃; for 0.05h;	98.5%
With Ta(η5-C5Me5)(η3-1-phenylallyl)2 In toluene for 12h; Ambient temperature;	63%
durch Zersetzung mit Wasser;
With hydrogen sulfide

S,S-dimethyl dithiocarbonate (868-84-8) + ethylamine (75-04-7) → N,N'-diethylurea (623-76-7)

Conditions	Yield
In water at 60℃; for 5h;	96%
at 100℃;

carbon monoxide (201230-82-2) + benzenenesulfenyl dimethylamine (6667-19-2) → N,N'-diethylurea (623-76-7) + N,N,N',N'-tetraethyloxamide (14288-05-2) + diethylamine (109-89-7) + diethylthiocarbamic acid S-phenyl ester

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0) In pyridine at 80℃; under 14701.2 Torr; for 10h; Carbonylation;	A n/a B 1.4 % Spectr. C 3 % Spectr. D 90%

ethylamine (75-04-7) + urea (57-13-6) → N,N'-diethylurea (623-76-7)

Conditions	Yield
With cerium(III) chloride; potassium iodide In water for 0.0666667h; microwave irradiation;	87%
at 140 - 150℃; Neat (no solvent);

carbon monoxide (201230-82-2) + N,N-diethyl-S-(3-methoxy-phenyl)-thiohydroxylamine → N,N'-diethylurea (623-76-7) + N,N,N',N'-tetraethyloxamide (14288-05-2) + diethylamine (109-89-7) + diethyl-thiocarbamic acid S-(3-methoxy-phenyl) ester

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0) In pyridine at 80℃; under 14701.2 Torr; for 3h; Carbonylation;	A n/a B 1.4 % Spectr. C 3 % Spectr. D 81%

N-Methylhydroxylamine (593-77-1) + ethyl isocyanate (109-90-0) → 1-ethyl-3-methylurea (28145-10-0) + N,N'-diethylurea (623-76-7)

Conditions	Yield
Stage #1: N-Methylhydroxylamine; ethyl isocyanate With magnesium oxide In acetone at 20℃; for 0.166667h; Stage #2: for 0.0583333h; Microwave irradiation; neat (no solvent);	A 74% B 10%

N-ethyl-2-(3-methylbenzo[d]thiazol-2(3H)-ylidene)hydrazinecarboxamide → N,N'-diethylurea (623-76-7) + 1,2-bis(3-methylbenzo[d]thiazol-2(3H)-ylidene)hydrazine (13545-63-6)

Conditions	Yield
at 220℃; under 0.5 Torr; for 0.5h;	A 73% B 67%

N-Phenylhydroxylamine (100-65-2) + ethyl isocyanate (109-90-0) → N,N'-diethylurea (623-76-7) + 1-ethyl-3-phenylurea (621-04-5)

Conditions	Yield
Stage #1: N-Phenylhydroxylamine; ethyl isocyanate With magnesium oxide In acetone at 20℃; for 0.166667h; Stage #2: for 0.0666667h; Microwave irradiation; neat (no solvent);	A 9% B 72%

N-Ethylimidazole (7098-07-9) + 2-cyano-1-phenylacetylene (935-02-4) + ethyl isocyanate (109-90-0) → N,N'-diethylurea (623-76-7) + N-[(Z)-2-cyano-1-phenylethenyl]-N,1-diethyl-1H-imidazole-2-carboxamide (1415219-02-1)

Conditions	Yield
In neat (no solvent) at 20 - 25℃; for 48h; Green chemistry; stereoselective reaction;	A 31% B 65%

1-methyl-1H-imidazole (616-47-7) + 2-cyano-1-phenylacetylene (935-02-4) + ethyl isocyanate (109-90-0) → N,N'-diethylurea (623-76-7) + (Z)-3-(1-methyl-1H-imidazol-2-yl)-3-phenyl-2-propenenitrile (1079368-39-0) + N-[(Z)-2-cyano-1-phenylethenyl]-N-ethyl-1-methyl-1H-imidazole-2-carboxamide (1415219-01-0)

Conditions	Yield
In neat (no solvent) at 20 - 25℃; for 24h; Green chemistry; stereoselective reaction;	A 33% B 10% C 50%

ethyl isocyanate (109-90-0) → N,N'-diethylurea (623-76-7) + C6H12N2O2 (101981-15-1)

Conditions	Yield
With hydrogen; In tetrahydrofuran at 120℃; under 37503 Torr; for 40h;	A n/a B 41%

methanol (67-56-1) + carbon monoxide (201230-82-2) + ethylamine (75-04-7) → methyl N-ethylcarbamate (6135-31-5) + N,N'-diethylurea (623-76-7)

Conditions	Yield
With dichloro bis(acetonitrile) palladium(II); triethylamine under 760 Torr; for 4h; Ambient temperature;	A 37% B 18%

carbon monoxide (201230-82-2) + ethylamine (75-04-7) → methyl N-ethylcarbamate (6135-31-5) + N,N'-diethylurea (623-76-7)

Conditions	Yield
With dichloro bis(acetonitrile) palladium(II); triethylamine In methanol under 760 Torr; for 4h; Ambient temperature;	A 37% B 18%

2-cyano-1-phenylacetylene (935-02-4) + 1-allylimidazole (31410-01-2) + ethyl isocyanate (109-90-0) → N,N'-diethylurea (623-76-7) + (Z)-3-(1-allyl-1H-imidazol-2-yl)-3-phenyl-2-propenenitrile (1079368-45-8) + 1-allyl-N-[(Z)-2-cyano-1-phenylethenyl]-N-ethyl-1H-imidazole-2-carboxamide (1415219-03-2)

Conditions	Yield
In neat (no solvent) at 20 - 25℃; for 24h; Green chemistry; stereoselective reaction;	A 31% B 37% C 28%

chloroform (67-66-3) + ethanamine hydrochloride (557-66-4) → N,N'-diethylurea (623-76-7)

Conditions	Yield
With oxygen; sodium hydroxide In water at 10℃; for 5h; Irradiation;	14%

propionyl azide (7139-74-4) → N,N'-diethylurea (623-76-7)

Conditions	Yield
With ethanol

ethylcarbamic 2-hydroxyethylester (18804-23-4) → N,N'-diethylurea (623-76-7)

Conditions	Yield
beim Erhitzen;

C8H17N3O2 → N,N'-diethylurea (623-76-7) + ethyl isocyanate (109-90-0)

N',N'''-diethyl-N,N''-m-phenylene-di-urea (39938-75-5) → N,N'-diethylurea (623-76-7)

Conditions	Yield
at 230℃;

N-ethyl-N'-biphenyl-4-yl-urea (871876-66-3) → N,N'-diethylurea (623-76-7) + 1,3-di([1,1'-biphenyl]-4-yl)urea (95745-38-3)

Conditions	Yield
at 290℃;

methyl O-methyldithiocarbonate (19708-81-7) + ethylamine (75-04-7) → N,N'-diethylurea (623-76-7)

Conditions	Yield
at 100℃;

S-phenyl N-ethylthiocarbamate (14467-74-4) + ethylamine (75-04-7) → N,N'-diethylurea (623-76-7)

Conditions	Yield
With ethanol

ethylamine (75-04-7) + ethyl isocyanate (109-90-0) → N,N'-diethylurea (623-76-7)

ethanamine hydrochloride (557-66-4) + urea (57-13-6) → N,N'-diethylurea (623-76-7)

Conditions	Yield
at 160 - 170℃;
at 150 - 170℃;

N,N'-diethylcarbodiimide (693-29-8) → N,N'-diethylurea (623-76-7)

Conditions	Yield
With hydrogenchloride

1,3-diethyluracil (22390-04-1) → N,N'-diethylurea (623-76-7)

Conditions	Yield
With tetramethyl ammoniumhydroxide In dimethyl sulfoxide

N-formylethylamine (627-45-2) + ethylamine (75-04-7) → N,N'-diethylurea (623-76-7)

Conditions	Yield
(i) IF5, Py, (ii) /BRN= 505933/, benzene; Multistep reaction;

carbon monoxide (201230-82-2) + ethylamine (75-04-7) → N,N'-diethylurea (623-76-7)

Conditions	Yield
With sulfur at 120℃;
With iodine; potassium carbonate; palladium diacetate In acetonitrile at 95℃; under 2052 Torr; for 3h;	75 % Chromat.

N-ethyl-N'-hydroxyurea (5710-11-2) → N,N'-diethylurea (623-76-7) + N-ethyl-N'-ethylaminocarbonyloxyurea (27108-44-7) + ethylamine (75-04-7)

Conditions	Yield
In acetonitrile Product distribution; Mechanism; Electrolysis of N-hydroxy- or N-alkoxy-ureas; the effect of divided or undivided cell and the excess of ethylamine or isopropylamine.;

N,N'-diethylurea (623-76-7) + (E)-1-(buta-1,3-dien-1-yl)-4-(trifluoromethyl)benzene (205108-18-5) → 1,3-Diethyl-4-[(E)-2-(4-trifluoromethyl-phenyl)-vinyl]-imidazolidin-2-one

Conditions	Yield
With dichloro bis(acetonitrile) palladium(II); p-benzoquinone In 1,2-dimethoxyethane at 60℃; for 48h;	100%

N,N'-diethylurea (623-76-7) + (E)-1-Phenyl-1,3-butadiene (16939-57-4) → 1,3-Diethyl-4-((E)-styryl)-imidazolidin-2-one

Conditions	Yield
With dichloro bis(acetonitrile) palladium(II); p-benzoquinone In 1,2-dimethoxyethane at 60℃; for 24h;	99%

N,N'-diethylurea (623-76-7) + malonic acid (141-82-2) → 1,3-diethylbarbituric acid (32479-73-5)

Conditions	Yield
With acetic anhydride; acetic acid at 60℃; for 6h;	97%
Stage #1: N,N'-diethylurea; malonic acid With acetic anhydride; acetic acid at 60℃; for 6h; Stage #2: In water at 70℃; for 0.5h;	65%

N,N'-diethylurea (623-76-7) + methyl 2-methylaminocyanoacetate → 1,3-diethyl-5-methylamino-6-aminouracil

Conditions	Yield
In 1,4-dioxane at 100 - 105℃; for 4h; Temperature;	95.8%

N-methylene-tert-butylamine (13987-61-6) + N,N'-diethylurea (623-76-7) → 5-tert-Butyl-1,3-diethyl-[1,3,5]triazinan-2-one (140367-28-8)

Conditions	Yield
for 4h; Heating;	94%

N,N'-diethylurea (623-76-7) + cyanoacetic acid (372-09-8) → 6-amino-1,3-diethyluracil (41740-15-2)

Conditions	Yield
Stage #1: N,N'-diethylurea; cyanoacetic acid In acetic anhydride at 75 - 85℃; for 2h; Inert atmosphere; Large scale; Stage #2: With sodium hydroxide at 5 - 10℃; for 1h; Large scale;	93.3%
With acetic anhydride at 80℃; for 2h;	88%
Stage #1: N,N'-diethylurea; cyanoacetic acid With acetic anhydride at 60℃; for 0.166667h; microwave irradiation; Stage #2: With sodium hydroxide In ethanol at 20℃;	70%

pyrimidine-2,4,5,6(1H,3H)-tetraone (61066-33-9, 61066-34-0, 61066-35-1, 61127-23-9) + N,N'-diethylurea (623-76-7) → 1,3-diethyl-4-hydroxy-2,5-dioxo-imidazolidine-4-carboxylic acid carbamoylamide (71886-26-5)

Conditions	Yield
In water at 90℃;	93%
With water

N,N'-diethylurea (623-76-7) + (4SR,5RS,6SR)-5-methyl-4-phenyl-6-(pyrrolidin-1-ylcarbonyl)cycloheptane-1,2-dione → C24H31N3O2

Conditions	Yield
With zinc trifluoromethanesulfonate In acetonitrile at 100℃; for 2h; Inert atmosphere; Molecular sieve; Sealed vial;	93%

N,N'-diethylurea (623-76-7) + (E)-3,4-dimethoxycinnamic chloride (39856-08-1, 141236-46-6) + ethyl 2-methylaminocyanoacetate → istradefylline (155270-99-8)

Conditions	Yield
Stage #1: N,N'-diethylurea; ethyl 2-methylaminocyanoacetate In 1,4-dioxane at 95 - 100℃; for 5h; Stage #2: With potassium hydroxide at 10 - 95℃; for 3h; Stage #3: (E)-3,4-dimethoxycinnamic chloride With triethylamine In 1,4-dioxane at 10 - 45℃; for 5h; Temperature;	90.9%

Glyoxal (131543-46-9) + N,N'-diethylurea (623-76-7) → 1,3-diethyl-4,5-dihydroxyimidazolidin-2-one (53629-29-1)

Conditions	Yield
With hydrogenchloride In water at 50℃; for 2h; pH=4 - 4.5;	90%
With sodium hydroxide at 50℃; for 7h; pH 5;	60%

N,N'-diethylurea (623-76-7) + carbon monoxide (201230-82-2) + cyclohexanecarbaldehyde (2043-61-0) → 5-cyclohexyl-1,3-diethyl-imidazolidine-2,4-dione

Conditions	Yield
With sulfuric acid; lithium bromide; bis(triphenylphosphine)palladium dibromide In 1-methyl-pyrrolidin-2-one at 100℃; under 45003.6 Torr; for 12h; Cyclization;	89%

oxalyl dichloride (79-37-8) + N,N'-diethylurea (623-76-7) → 1-ethyl-2,4,5-trioxoimidazolidine (57012-86-9)

Conditions	Yield
With benzene at 20℃;	85%

N,N'-diethylurea (623-76-7) + 2,3-dimethyl-buta-1,3-diene (513-81-5) → 1,3-diethyl-4-isopropenyl-4-methyl-imidazolidin-2-one

Conditions	Yield
With dichloro bis(acetonitrile) palladium(II); p-benzoquinone In 1,2-dimethoxyethane at 60℃; for 24h;	82%

phthalic anhydride (85-44-9) + 5-fluoro-1H-indole-2,3-dione (443-69-6) + N,N'-diethylurea (623-76-7) → 5-hydroxy-5-(5-fluoro-2-(isoindolin-2-yl-1,3-dione)phenyl)-1,3-diethylhydantoin

Conditions	Yield
With toluene-4-sulfonic acid In acetonitrile at 80℃; for 5h;	82%

N,N'-diethylurea (623-76-7) + isoprene (78-79-5) → 1,3-diethyl-4-isopropenyl-imidazolidin-2-one + 1,3-diethyl-4-methyl-4-vinyl-imidazolidin-2-one

Conditions	Yield
With dichloro bis(acetonitrile) palladium(II); p-benzoquinone In 1,2-dimethoxyethane at 60℃; for 24h; Title compound not separated from byproducts;	A 81% B n/a

dibromomethylborane (17933-16-3) + N,N'-diethylurea (623-76-7) → 3,5-Diethyl-2,3,5,6-tetrahydro-2,6-dimethyl-4H-1,3,5,2,6-oxadiazadiborin-4-on (81233-27-4) + 2-Methyl-1,3,5-triethyl-1,3,5-triaza-2-bora-cyclohexandion-4,6

Conditions	Yield
In tetrachloromethane byproducts: HBr; edducts refluxed under N2 in 1:1 ratio for 24 h; evapd. in vac., distd. in vac., elem. anal.;	A n/a B 81%

succinic acid anhydride (108-30-5) + 5-fluoro-1H-indole-2,3-dione (443-69-6) + N,N'-diethylurea (623-76-7) → 5-hydroxy-5-(5-fluoro-2-(pyrrolidin-1-yl-2,5-dione)phenyl)-1,3-diethylhydantoin

Conditions	Yield
With toluene-4-sulfonic acid In acetonitrile at 80℃; for 5h;	81%

phthalic anhydride (85-44-9) + N,N'-diethylurea (623-76-7) + 5-chloroindole 2,3-dione (17630-76-1) → 5-hydroxy-5-(5-chloro-2-(isoindolin-2-yl-1,3-dione)phenyl)-1,3-diethylhydantoin

Conditions	Yield
With toluene-4-sulfonic acid In acetonitrile at 80℃; for 5h;	81%

N,N'-diethylurea (623-76-7) → ethylnitramine (19091-98-6)

Conditions	Yield
With fuming sulphuric acid; nitric acid In dichloromethane at -5 - 20℃; for 1h; Temperature;	80.6%

formaldehyd (50-00-0) + N,N'-diethylurea (623-76-7) + H-Phe-OEt (3081-24-1) → (S)-2-(3,5-Diethyl-4-oxo-[1,3,5]triazinan-1-yl)-3-phenyl-propionic acid ethyl ester (130750-10-6)

Conditions	Yield
In water at 70 - 110℃;	80%

formaldehyd (50-00-0) + N,N'-diethylurea (623-76-7) + L-serine ethyl ester hydrochloride (26348-61-8) → 5-<1-(S)-(1-Carbethoxy-2-hydroxy)ethyl>-1,3-diethyl-hexahydro-2-oxo-1,3,5-triazine (130767-32-7)

Conditions	Yield
With triethylamine In ethanol; water for 20h; Heating;	80%

N,N'-diethylurea (623-76-7) + (E)-1-(buta-1,3-diene-1-yl)-4-methoxybenzene (32507-39-4) → 1,3-Diethyl-4-[(E)-2-(4-methoxy-phenyl)-vinyl]-imidazolidin-2-one

Conditions	Yield
With dichloro bis(acetonitrile) palladium(II); p-benzoquinone In 1,2-dimethoxyethane at 60℃; for 24h;	80%

phthalic anhydride (85-44-9) + 5-methyl-indole-2,3-dione (608-05-9) + N,N'-diethylurea (623-76-7) → 5-hydroxy-5-(5-methyl-2-(isoindolin-2-yl-1,3-dione)phenyl)-1,3-diethylhydantoin

Conditions	Yield
With toluene-4-sulfonic acid In acetonitrile at 80℃; for 5h;	80%

dibromomethylborane (17933-16-3) + N,N'-diethylurea (623-76-7) → tributyl borane (122-56-5) + 3,5-Diethyl-2,3,5,6-tetrahydro-2,6-dimethyl-4H-1,3,5,2,6-oxadiazadiborin-4-on (81233-27-4)

Conditions	Yield
With n-butyllithium In hexane; Petroleum ether byproducts: butane, LiBr; the urea in petroleum ether was refluxed under N2 with n-BuLi in hexanefor 48 h; the solvents were removed in vac., the residue was fractional distd.; elem. anal.;	A n/a B 79%

Upstream product

• 7139-74-4 propionyl azide 
• 18804-23-4 ethylcarbamic 2-hydroxyethylester 
• 39938-75-5 N',N'''-diethyl-N,N''-m-phenylene-di-urea 
• 871876-66-3 N-ethyl-N'-biphenyl-4-yl-urea 
• 868-84-8 S,S-dimethyl dithiocarbonate 
• 75-04-7 ethylamine 
• 19708-81-7 methyl O-methyldithiocarbonate 
• 14467-74-4 S-phenyl N-ethylthiocarbamate 
• 109-90-0 ethyl isocyanate 
• 693-29-8 N,N'-diethylcarbodiimide 
• 22390-04-1 1,3-diethyluracil 
• 627-45-2 N-formylethylamine 
• 201230-82-2 carbon monoxide 
• 5710-11-2 N-ethyl-N'-hydroxyurea 

Downstream Products

• 625-50-3 N-ethylacetamide 
• 41740-15-2 6-amino-1,3-diethyluracil 
• 62517-26-4 1-{2-Chloro-3-[4-(2-methyl-2-phenyl-propoxy)-phenyl]-propionyl}-1,3-diethyl-urea 
• 1467-23-8 N-(ethylcarbamoyl)-4-methylbenzenesulfonamide 
• 21243-32-3 N',N'-Dimethyl-N-ethylurea 
• 130750-10-6 (S)-2-(3,5-Diethyl-4-oxo-[1,3,5]triazinan-1-yl)-3-phenyl-propionic acid ethyl ester 
• 75-04-7 ethylamine 
• 73633-54-2 1,3-diethyl-2-oxo-5-phenyltetrahydroimidazole-4-spiro-4'-(1',3'-diethyltetrahydroimidazole-2'-one) 
• 53629-29-1 1,3-diethyl-4,5-dihydroxyimidazolidin-2-one 
• 78994-41-9 (Z)-4-(ethylamino)pent-3-en-2-one 
• 49540-32-1 N-nitroso-1,3-diethylurea 
• 557-66-4 ethanamine hydrochloride 
• 109-90-0 ethyl isocyanate 
• 603-54-3 N,N-diphenylurea 

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The objective of the present invention is to provide a method for producing a carbonate derivative in a safe and efficient manner. The method for producing a carbonate derivative according to the present invention is characterized in comprising irradiating light on a composition containing a C1-4 halogenated hydrocarbon having one or more kinds of halogen atoms selected from the group consisting of a chlorine atom, a bromine atom and an iodine atom, a nucleophilic functional group-containing compound and the specific base in the presence of oxygen.

PROCESS FOR PREPARING CYCLIC ALKYLENE UREAS

A process for producing a cyclic alkylene urea product of Formula I: in which a compound of Formula II and/or Formula III is contacted in a reaction zone with a compound of Formula IV and/or Formula V and in the presence of one or more carbonyl delivering compounds; in which; R1 is –[A?X?]qR3; R2 is on each occurrence independently selected from H and C1 to C6 alkyl groups which are optionally substituted by one or two groups selected from ?OH and ?NH2; R3 is on each occurrence independently selected from H and C1 to C6 alkyl groups which are optionally substituted by one or two groups selected from ?OH and ?NH2; A is on each occurrence independently selected from C1 to C3 alkylene units, optionally substituted by one or more C1 to C3 alkyl groups; X is on each occurrence independently selected from ?O?, ?NR2?, groups of Formula VI, and groups of Formula VII and p and q are each independently selected from a whole number in the range of from 0 to 8; wherein the compound of Formula II and/or the compound of Formula III are added to a reaction zone comprising compound of Formula IV and/or compound of Formula (V) continuously or semi-continuously over a period of time, or in two or more batches.

Synthesis, thermolysis, photolysis and antimicrobial evaluation of some novel semicarbazones and thiosemicarbazones derived from 3-methyl-2-benzothiazolinone hydrazone

REACTION of 3-methyl-2-benzothiazolinone hydrazone (1) with?? some selected isocyanate and isothiocyanate reagents 2a-j gave the respective semicarbazones and thiosemicarbazones 3a-j. Thermolysis of compound 3a under reduced pressure gave N,N'-diethylurea (4) in addition to 1,2-bis(3-methylbenzo[d]thiazol-2(3H)-ylidene)hydrazine (5). Compound 3a was almost quantitatively recovered upon its exposure to sunlight in methanol for 60 days. Elementary and spectroscopic measurements (IR, 1H NMR, 13C NMR, MS) are in good accord with the structures postulated for the new compounds. The single crystal X-ray crystallographic analysis of 3f was given and its data were discussed. The synthesized compounds 3aj as well as the hydrazone 1 were screened for their antibacterial properties against Bacillus subtilis (G+), Escherichia coli (G-), Pseudomonas aeruginosa (G-) and Staphylococcus aureus (G+) and for their antifungal properties against Aspergillus flavus and Candida albicans. Some of the tested compounds showed an activity against the four bacterial strains where their order of activity was found to be 1 > 3g > 3j > 3i > 3e > 3h > 3a. The MIC90 value of compound 1 against P. aeruginosa was 9 mg/ml. On the other hand only compound 1 showed a significant activity against A. flavus fungal species where it recorded an inhibition zone diameter value (16 mm/mg) which is very near to that of the standard drug, amphotericin B (17 mm/mg). However, the C. albicans was found to be insensitive to all of the investigated compounds.

Microwave-assisted synthesis of symmetrical and unsymmetrical N,N 0-disubstituted thioureas and ureas over MgO in dry media

Under mild microwave irradiation conditions a variety of symmetrical and unsymmetrical A,N′-disubsti-tuted thioureas and ureas were prepared via the reaction of Af-monosubstituted hydroxylamines with isocyanate and isothiocyanate derivatives over MgO under solvent-free conditions. This new method afforded satisfactory results with good yields, short reaction time, and simplicity in the experimental procedure.

Three-component reaction between imidazoles, isocyanates, and cyanophenylacetylene: A short-cut to N-(Z)-alkenylimidazole-2-carboxamides

1-Substituted imidazoles, isocyanates, and cyanophenylacetylene react under mild (rt), non-catalytic solvent-free conditions to give (Z)-(2-cyano-1- phenylethenyl)imidazole-2-carboxamides in up to 72% yields and with ca. 100% stereoselectivity. The reaction starts from the initial formation of zwitterion/carbene intermediates captured by the isocyanate as the electrophile followed by migration of the alkenyl moiety from the N-3 atom to the anionic center at the carboxamide nitrogen. Thus, the reaction provides an easy access to a novel family of functionalized imidazoles.

PROCESS FOR STRAIGHTENING KERATIN FIBRES WITH A HEATING MEANS AND DENATURING AGENTS

The invention relates to a process for straightening keratin fibres, comprising: (i) a step in which a straightening composition containing at least two denaturing agents is applied to the keratin fibres, (ii) a step in which the temperature of the keratin fibres is raised, using a heating means, to a temperature of between 110 and 250° C.

4,5-Dihydroxyimidazolidin-2-ones in the α-ureidoalkylation reaction of N-(carboxyalkyl)-, N-(hydroxyalkyl)-, and N-(aminoalkyl)ureas 1. α-Ureidoalkylation of N-(carboxyalkyl)ureas

The α-ureidoalkylation of N-(carboxyalkyl)ureas (ureido acids) with 1,3-H2 s-, 1,3-Me 2 s-, and 1,3-Et2 s-4,5-dihydroxyimidazolidin-2-ones was systematically studied. The yields of glycolur

Preparation of mono-, di-, and trisubstituted ureas by carbonylation of aliphatic amines with S,S-dimethyl dithiocarbonate

General procedures are reported to prepare N-alkylureas, N,N′-dialkylureas (both symmetrical and unsymmetrical), and N,N,N′-trialkylureas by carbonylation of aliphatic amines, employing S,S-dimethyl dithiocarbonate (DMDTC) as a phosgene substitute. All reactions were carried out in water. Symmetrical disubstituted ureas were prepared directly working at 60°C with a molar ratio of DMDTC:amine = 1:2, preferably under nitrogen. Unsymmetrical ureas were prepared in two steps via S-methyl N-alkyl-thiocarbamate intermediates, which are formed selectively in the first step at room temperature. These intermediates react in the second step with ammonia or various aliphatic amines, both primary and secondary, at temperatures varying between 50 and 70°C. All the target ureas were obtained in high yields (28 examples, average yield 94%) and with very high purity (generally >99.2%). Also to be noted is the recovery of a co-product of industrial interest, methanethiol, in an amount of two moles for each mole of DMDTC, with complete exploitation of the reagent. Georg Thieme Verlag Stuttgart.

Expeditious method for synthesis of symmetrical 1,3-disubstituted ureas and thioureas

Symmetrical 1,3-disubstituted ureas and symmetrical thioureas have been synthesized from corresponding isocyanates, diisocyanates, and isothiocyanates by a new versatile, simple, and quick method in the presence of tertiary amines at room temperature. The method under discussion has several advantages over the existing techniques, as it is simple to carry out, does not require complicated equipment, has a simple workup, and does not use expensive chemicals. Moreover, the yields are almost quantitative. This method has potential in commercial applications. Copyright Taylor & Francis, Inc.