4-Ethyl-2,3-dioxo-1-piperazine carbonyl chloride supplier

Name
4-Ethyl-2,3-dioxo-1-piperazine carbonyl chloride
EINECS 261-867-0
CAS No. 59703-00-3
Article Data8
CAS DataBase
Density 1.408 g/cm³
Solubility decomposes
Melting Point 100 °C
Formula C₇H₉ClN₂O₃
Boiling Point 292.9 °C at 760 mmHg
Molecular Weight 204.613
Flash Point 131 °C
Transport Information
Appearance White to tan powder, partially agglomerated
Safety 45-36/37/39-26
Risk Codes 34
Molecular Structure
Hazard Symbols C
Synonyms 4-ethyl-2,3-dioxopiperazin-1-carbonylchlorid;
PSA 57.69000
LogP -0.08830

Synthetic route

: 32315-10-9
bis(trichloromethyl) carbonate

: 59702-31-7
1-ethyl-2,3-dioxo-piperazine

: 59703-00-3
4-ethyl-2,3-dioxopiperazine-1-carbonyl chloride

Conditions

Conditions	Yield
With pyridine; dmap; chloro-trimethyl-silane In dichloromethane at -25 - -20℃;	94.3%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 10 - 20℃; for 1.06667h; Temperature; Reagent/catalyst; Green chemistry;	93.9%
Stage #1: 1-ethyl-2,3-dioxo-piperazine With chloro-trimethyl-silane; triethylamine In dichloromethane at 0 - 20℃; for 1h; Inert atmosphere; Schlenk technique; Stage #2: bis(trichloromethyl) carbonate In dichloromethane at -30℃; Inert atmosphere; Schlenk technique;

: 75-44-5
phosgene

: 59702-31-7
1-ethyl-2,3-dioxo-piperazine

: 59703-00-3
4-ethyl-2,3-dioxopiperazine-1-carbonyl chloride

Conditions

Conditions	Yield
With chloro-trimethyl-silane; triethylamine In tetrahydrofuran; 1,4-dioxane

: 149-30-4
2-Mercaptobenzothiazole

A: 120600-74-0
S-2-benzothiazolyl-4-ethyl-2,3-dioxo-1-piperazinethio-carboxylate

B: 59703-00-3
4-ethyl-2,3-dioxopiperazine-1-carbonyl chloride

Conditions

Conditions	Yield
With triethylamine In dichloromethane

: 69-53-4
ampicillin

: 59703-00-3
4-ethyl-2,3-dioxopiperazine-1-carbonyl chloride

: 61477-96-1, 64131-97-1
piperacillin

Conditions

Conditions	Yield
With calcium carbonate In dichloromethane; water; ethyl acetate at 30 - 35℃; for 0.833333h;	93.7%
With sodium acetate; 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane; water; ethyl acetate at 5 - 10℃; for 0.916667h; pH=6.5 - 7.5; Temperature; Reagent/catalyst; Green chemistry;	92.8%
With triethylamine In water; ethyl acetate at 15 - 20℃; for 1h; pH=7.1;	123.5 g

: 72292-40-1, 72345-50-7, 72377-68-5
7β-<(2R)-2-phenyl-2-amino>acetylamino-1-carba-1-dethia-3-cephem-4-carboxylic acid

: 59703-00-3
4-ethyl-2,3-dioxopiperazine-1-carbonyl chloride

: 72292-42-3, 72401-86-6
7β-<(2R)-2-phenyl-2-(4-ethyl-2,3-dioxopiperazine-1-yl-carbonyl)amino>acetylamino-1-carba-1-dethia-3-cephem-4-carboxylic acid

Conditions

Conditions	Yield
	93%

: 3228-02-2
3-Methyl-4-isopropylphenol

: 59703-00-3
4-ethyl-2,3-dioxopiperazine-1-carbonyl chloride

: 4-isopropyl-3-methylphenyl N-(4-ethyl-2,3-dioxo-1-piperazine)carbamate

Conditions

Conditions	Yield
With triethylamine In acetonitrile at 20℃; for 4h;	92%

: 632-20-2
D-Threonine

: 59703-00-3
4-ethyl-2,3-dioxopiperazine-1-carbonyl chloride

: C11H17N3O6

Conditions

Conditions	Yield
With sodium carbonate In water at 20℃; for 11h; Reagent/catalyst; Solvent; Large scale;	90.2%

: 73910-33-5
7β-<(2R)-2-phenyl-2-amino>acetylamino-3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid

: 59703-00-3
4-ethyl-2,3-dioxopiperazine-1-carbonyl chloride

: 73910-34-6
7β-<(2R)-2-phenyl-2-(4-ethyl-2,3-dioxopiperazin-1-yl-carbonyl)amino>acetylamino-3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-1-carba-1-dethia-3-cephem-4-carboxylic acid

Conditions

Conditions	Yield
With benzenesulfonamide; methyloxirane In acetonitrile for 0.416667h;	90%

: 1-Ethyl-4-trimethylsilanyl-piperazine-2,3-dione

: 59703-00-3
4-ethyl-2,3-dioxopiperazine-1-carbonyl chloride

: N,N'-carbonyl-bis-(4-ethyl-2,3-dioxopiperazine)

Conditions

Conditions	Yield
In dichloromethane at -5 - 25℃; for 8.67h; Solvent;	84%

: 22818-40-2
D-4-hydroxyphenylglycine

: 59703-00-3
4-ethyl-2,3-dioxopiperazine-1-carbonyl chloride

: 62893-24-7
(R)-<<(4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl>amino>(4-hydroxyphenyl)acetic acid

Conditions

Conditions	Yield
With sodium carbonate; zinc dibromide In water at 200℃; for 3h; Temperature; Reagent/catalyst; Autoclave;	83.5%

: 72699-69-5
α-amino-α-(2-benzyloxycarbonylaminothiazol-4-yl)acetic acid

: 59703-00-3
4-ethyl-2,3-dioxopiperazine-1-carbonyl chloride

: 85208-16-8
(+/-)-α-(2-benzyloxycarbonylaminothiazol-4-yl)-α-(4-ethyl-2,3-dioxopiperazin-1-ylcarbonylamino)acetic acid

Conditions

Conditions	Yield
With triethylamine In acetone for 1h; Ambient temperature;	69%

: 88585-78-8
<4S,5R,6S(R)>-3-(hydroxymethyl)-6-<1-<(tert-butyldimethylsilyl)oxy>ethyl>-7-oxo-4-thia-1-azabicyclo<3.2.0>hept-2-enecarboxylic acid 2-allyl ester

: 59703-00-3
4-ethyl-2,3-dioxopiperazine-1-carbonyl chloride

: (5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-(4-ethyl-2,3-dioxo-piperazine-1-carbonyloxymethyl)-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester

Conditions

Conditions	Yield
With N,N-diethyl-N-isopropylamine In dichloromethane	51%

: 59-92-7
levodopa

: 59703-00-3
4-ethyl-2,3-dioxopiperazine-1-carbonyl chloride

: 263154-16-1
(S)-3-(3,4-Dihydroxy-phenyl)-2-[(4-ethyl-2,3-dioxo-piperazine-1-carbonyl)-amino]-propionic acid

Conditions

Conditions	Yield
Stage #1: levodopa With chloro-trimethyl-silane; 1,1,1,3,3,3-hexamethyl-disilazane for 2h; silylation; Heating; Stage #2: 4-ethyl-2,3-dioxopiperazine-1-carbonyl chloride In dichloromethane at 20℃; for 1.5h; Acylation; Stage #3: With water In acetone for 0.3h; pH=1 - 2; desilylation;	49%

: C18H19N7O5S2

: 59703-00-3
4-ethyl-2,3-dioxopiperazine-1-carbonyl chloride

: 62893-19-0, 68779-10-2
cefoperazone

Conditions

Conditions	Yield
With potassium carbonate In water; ethyl acetate at 20℃;	42%

: D-3,4-Dihydroxyphenyl glycine

: 59703-00-3
4-ethyl-2,3-dioxopiperazine-1-carbonyl chloride

: 74985-17-4
D-2-[(4-Ethyl-2,3-dioxopiperazin-1-yl)carbonylamino]-2-(3,4-dihydroxyphenyl)acetic acid

Conditions

Conditions	Yield
With chloro-trimethyl-silane In dichloromethane; water; acetone; 1,1,1,3,3,3-hexamethyl-disilazane	40%
With hydrogenchloride In diethyl ether; dichloromethane; ethyl acetate; acetone; N,N-diethyl-1,1,1-trimethylsilanamine	27%

: 2-(3-{[5-(2-aminoethoxy)benzothiazol-2-ylmethyl]amino}-[1,2,4]triazin-5-yl)-3-methylphenol hydrochloride

: 59703-00-3
4-ethyl-2,3-dioxopiperazine-1-carbonyl chloride

: 1426097-00-8
C27H28N8O5S

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0℃; Inert atmosphere;	29%

: t-butyl 7β-(D-2-amino-2-phenylacetamido)-7α-formamidocephalosporanate

: 59703-00-3
4-ethyl-2,3-dioxopiperazine-1-carbonyl chloride

: t-Butyl 7β-[D-2-[(4-Ethyl-2,3-dioxopiperazin-1-yl)carbonylamino]-2-phenylacetamido]-7α-formamidocephalosporanate

Conditions

Conditions	Yield
With pyridine In dichloromethane	22%

: 1364569-65-2
4-(aminomethyl)-N-(2-nitro-5-(thiophen-2-yl)phenyl)benzamide hydrochloride

: 59703-00-3
4-ethyl-2,3-dioxopiperazine-1-carbonyl chloride

: 1364569-75-4
4-ethyl-N-(4-(2-nitro-5-(thiophen-2-yl)phenylcarbamoyl)benzyl)-2,3-dioxopiperazine-1-carboxamide

Conditions

Conditions	Yield
With triethylamine In dichloromethane; N,N-dimethyl-formamide at 20℃;	22%

: 85208-10-2
6-<(+/-)-α-amino-α-(2-aminothiazol-4-yl)acetamido>penicillanic acid

: 59703-00-3
4-ethyl-2,3-dioxopiperazine-1-carbonyl chloride

A: 85208-19-1, 85208-20-4, 85280-44-0
6-<(+/-)-α-(2-aminothiazol-4-yl)-α-(4-ethyl-2,3-dioxopiperazin-1-ylcarbonylamino)acetamido>penicillanic acid

B: 59702-31-7
1-ethyl-2,3-dioxo-piperazine

Conditions

Conditions	Yield
With sodium hydrogencarbonate 1.) THF, H2O, 0 deg C, 2.) pH=7-7.5, room temperature, 1 h;	A 21% B n/a

...Expand

: (4R,8S)-8-(E)-2-amino-1-(((tert-butyldimethylsilyl)oxy)imino)ethyl-5-(benzyloxy)-1-methyl-1,4,5,8-tetrahydro-6H-4,7-methanopyrazolo[3,4-e][1,3]diazepin-6-one

: 59703-00-3
4-ethyl-2,3-dioxopiperazine-1-carbonyl chloride

: N-((E)-2-((4R,8S)-5-(benzyloxy)-1-methyl-6-oxo-4,5,6,8-tetrahydro-1H-4,7-methanopyrazolo[3,4-e][1,3]diazepin-8-yl)-2-(((tert-butyldimethylsilyl)oxy)imino)ethyl)-4-ethyl-2,3-dioxopiperazine-1-carboxamide

Conditions

Conditions	Yield
With pyridine; triethylamine at 20℃; for 0.333333h;	18.4%

: 73910-42-6
7β-<(2R)-2-phenyl-2-amino>acetylamino-3-methoxy-1-carba-1-dethia-3-cephem-4-carboxylic acid

: 59703-00-3
4-ethyl-2,3-dioxopiperazine-1-carbonyl chloride

: 73910-43-7
7β-<(2R)-2-phenyl-2-(4-ethyl-2,3-dioxopiperazin-1-yl-carbonyl)amino>acetylamino-3-methoxy-1-carba-1-dethia-3-cephem-4-carboxylic acid

Conditions

Conditions	Yield
With benzenesulfonamide; methyloxirane In acetonitrile	15 mg

: 161855-50-1
CL191,121

: 59703-00-3
4-ethyl-2,3-dioxopiperazine-1-carbonyl chloride

: (4R,5S,6S)-3-((2R,3R)-2-{[(4-Ethyl-2,3-dioxo-piperazine-1-carbonyl)-amino]-methyl}-tetrahydro-furan-3-ylsulfanyl)-6-((R)-1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane

: (4R,5S,6S)-3-(5-Aminomethyl-tetrahydro-furan-3-ylsulfanyl)-6-((R)-1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid

: 59703-00-3
4-ethyl-2,3-dioxopiperazine-1-carbonyl chloride

: Sodium; (4R,5S,6S)-3-(5-{[(4-ethyl-2,3-dioxo-piperazine-1-carbonyl)-amino]-methyl}-tetrahydro-furan-3-ylsulfanyl)-6-((R)-1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylate

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane

: α-amino(3,4-dihydroxyphenyl)acetic acid hydrobromide

: 59703-00-3
4-ethyl-2,3-dioxopiperazine-1-carbonyl chloride

: 74985-17-4
D-2-[(4-Ethyl-2,3-dioxopiperazin-1-yl)carbonylamino]-2-(3,4-dihydroxyphenyl)acetic acid

Conditions

Conditions	Yield
Stage #1: α-amino(3,4-dihydroxyphenyl)acetic acid hydrobromide With chloro-trimethyl-silane; 1,1,1,3,3,3-hexamethyl-disilazane for 2h; silylation; Heating; Stage #2: 4-ethyl-2,3-dioxopiperazine-1-carbonyl chloride In dichloromethane at 20℃; for 1.5h; Acylation; Stage #3: With water In acetone for 0.3h; pH=1 - 2; desilylation;

: 5796-17-8
D-Dopa

: 59703-00-3
4-ethyl-2,3-dioxopiperazine-1-carbonyl chloride

: (R)-3-(3,4-Dihydroxy-phenyl)-2-[(4-ethyl-2,3-dioxo-piperazine-1-carbonyl)-amino]-propionic acid

Conditions

Conditions	Yield
Stage #1: D-Dopa With chloro-trimethyl-silane; 1,1,1,3,3,3-hexamethyl-disilazane for 2h; silylation; Heating; Stage #2: 4-ethyl-2,3-dioxopiperazine-1-carbonyl chloride In dichloromethane at 20℃; for 1.5h; Acylation; Stage #3: With water In acetone for 0.3h; pH=1 - 2; desilylation;

: 59703-00-3
4-ethyl-2,3-dioxopiperazine-1-carbonyl chloride

: (3,4-dihydroxy-phenyl)-[(4-ethyl-2,3-dioxo-piperazine-1-carbonyl)-amino]-acetic acid 2,5-dioxo-pyrrolidin-1-yl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 1,1,1,3,3,3-hexamethyldisilazane; trimethylsilyl chloride / 2 h / Heating 1.2: CH2Cl2 / 1.5 h / 20 °C 1.3: water / acetone / 0.3 h / pH 1 - 2 2.1: DCC / tetrahydrofuran / 2 h View Scheme

: 59703-00-3
4-ethyl-2,3-dioxopiperazine-1-carbonyl chloride

: (R)-3-(3,4-Dihydroxy-phenyl)-2-[(4-ethyl-2,3-dioxo-piperazine-1-carbonyl)-amino]-propionic acid 2,5-dioxo-pyrrolidin-1-yl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 1,1,1,3,3,3-hexamethyldisilazane; trimethylsilyl chloride / 2 h / Heating 1.2: CH2Cl2 / 1.5 h / 20 °C 1.3: water / acetone / 0.3 h / pH 1 - 2 2.1: DCC / tetrahydrofuran / 2 h View Scheme

: 59703-00-3
4-ethyl-2,3-dioxopiperazine-1-carbonyl chloride

: (S)-3-(3,4-Dihydroxy-phenyl)-2-[(4-ethyl-2,3-dioxo-piperazine-1-carbonyl)-amino]-propionic acid 2,5-dioxo-pyrrolidin-1-yl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 1,1,1,3,3,3-hexamethyldisilazane; trimethylsilyl chloride / 2 h / Heating 1.2: CH2Cl2 / 1.5 h / 20 °C 1.3: 49 percent / water / acetone / 0.3 h / pH 1 - 2 2.1: DCC / tetrahydrofuran / 2 h View Scheme

: 59703-00-3
4-ethyl-2,3-dioxopiperazine-1-carbonyl chloride

: (2S,3S)-3-{2-(3,4-Dihydroxy-phenyl)-2-[(4-ethyl-2,3-dioxo-piperazine-1-carbonyl)-amino]-acetylamino}-2-methyl-4-oxo-azetidine-1-sulfonic acid; compound with triethyl-amine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 1,1,1,3,3,3-hexamethyldisilazane; trimethylsilyl chloride / 2 h / Heating 1.2: CH2Cl2 / 1.5 h / 20 °C 1.3: water / acetone / 0.3 h / pH 1 - 2 2.1: DCC / tetrahydrofuran / 2 h 3.1: 61 mg / tetrahydrofuran; H2O / 3 h / 20 °C View Scheme

: 59703-00-3
4-ethyl-2,3-dioxopiperazine-1-carbonyl chloride

: (2S,3S)-3-{(S)-3-(3,4-Dihydroxy-phenyl)-2-[(4-ethyl-2,3-dioxo-piperazine-1-carbonyl)-amino]-propionylamino}-2-methyl-4-oxo-azetidine-1-sulfonic acid; compound with triethyl-amine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 1,1,1,3,3,3-hexamethyldisilazane; trimethylsilyl chloride / 2 h / Heating 1.2: CH2Cl2 / 1.5 h / 20 °C 1.3: 49 percent / water / acetone / 0.3 h / pH 1 - 2 2.1: DCC / tetrahydrofuran / 2 h 3.1: 84 percent / tetrahydrofuran; H2O / 3 h / 20 °C View Scheme

: 59703-00-3
4-ethyl-2,3-dioxopiperazine-1-carbonyl chloride

: (2S,3S)-3-{(R)-3-(3,4-Dihydroxy-phenyl)-2-[(4-ethyl-2,3-dioxo-piperazine-1-carbonyl)-amino]-propionylamino}-2-methyl-4-oxo-azetidine-1-sulfonic acid; compound with triethyl-amine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 1,1,1,3,3,3-hexamethyldisilazane; trimethylsilyl chloride / 2 h / Heating 1.2: CH2Cl2 / 1.5 h / 20 °C 1.3: water / acetone / 0.3 h / pH 1 - 2 2.1: DCC / tetrahydrofuran / 2 h 3.1: 129 mg / tetrahydrofuran; H2O / 3 h / 20 °C View Scheme

4-Ethyl-2,3-dioxo-1-piperazine carbonyl chloride Chemical Properties

IUPAC Name: 4-ethyl-2,3-dioxopiperazine-1-carbonyl chloride
Molecular Formula:C₇H₉ClN₂O₃
Molecular Weight:204.610960 g/mol
Appearance:white crystal
Melting Point:100 °C
Water Solubility:decomposes
CAS DataBase Reference:59703-00-3(CAS DataBase Reference)
Synonyms of 4-ETHYL-2,3-DIOXO-1-PIPERAZINECARBONYLCHLORIDE(59703-00-3):
edpc;1-CHLOROCARBONYL-4-ETHYL-2,3-DIOXOPIPERAZINE;4-ETHYL-2,3-DIOXO-1-PIPERAZINECARBONYL CHLORIDE;4-ETHYL-2,3-DIOXO-PIPERAZINE-1-CARBONYL CHLORIDE;4-ETHYL-2,3-DIOXO-PIPERAZINE CARBONYL CHLORIDE;N-Ethyl-2,3-dioxypiperazine-1-carbonylchloride;N-Ethyl-2,3-dioxo-1-piperazinecarbonyl chloride;4-Ethyl-2,3-dioxo-1-piperazine carbonyl chlorides
Categories of 4-ETHYL-2,3-DIOXO-1-PIPERAZINECARBONYLCHLORIDE(59703-00-3):
Piperaizine;Piperazine derivates;Cefoperazone

4-Ethyl-2,3-dioxo-1-piperazine carbonyl chloride Uses

4-ETHYL-2,3-DIOXO-1-PIPERAZINECARBONYLCHLORIDE(59703-00-3) is an important pharmaceutical intermediate mainly used for synthesis of Piperacillin and cefoperazone, etc.

4-Ethyl-2,3-dioxo-1-piperazine carbonyl chloride Safety Profile

Safety Information of 4-ETHYL-2,3-DIOXO-1-PIPERAZINECARBONYLCHLORIDE(59703-00-3):
Hazard Codes:C
Risk Statements:34
34:Causes burns
Safety Statements:45-36/37/39-26
45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
36/37/39:Wear suitable protective clothing, gloves and eye/face protection
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice

Product Name

4-Ethyl-2,3-dioxo-1-piperazine carbonyl chloride

Synthetic route

4-Ethyl-2,3-dioxo-1-piperazine carbonyl chloride Chemical Properties

4-Ethyl-2,3-dioxo-1-piperazine carbonyl chloride Uses

4-Ethyl-2,3-dioxo-1-piperazine carbonyl chloride Safety Profile

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