1558-82-3

Basic information

• Product Name: Ethyl N-cyanoethanimideate
• Synonyms: n-cyanoethanimidic acid ethyl ester;N-CYANOETHANIMIDIC ETHYL ESTER;ETHYLN-CYANOACETOIMIDATE;ETHYL N-CYANO ETHANIMIDATE;Ethyl N-cyanoethanimideate;CYANO ETHYL ACETAMIDATE;N-cyanoacetimidic acid ethyl ester;Ethyl N-cyanoacetiMidate
• CAS NO: 1558-82-3
• Molecular Formula: C₅H₈N₂O
• Molecular Weight: 112.13
• Mol File: 1558-82-3.mol
• Article Data: 9

Chemical Properties

• Melting Point: 78-81 °C(Solv: ethyl ether (60-29-7))
• Boiling Point: 133.2 °C at 760 mmHg
• Flash Point: 34.358 °C
• Appearance: /
• Density: 0.943 g/cm³
• Vapor Pressure: 8.561mmHg at 25°C
• Refractive Index: 1.444
• Storage Temp.: 2-8°C
• PKA: -2.94±0.50(Predicted)
• CAS DataBase Reference: Ethyl N-cyanoethanimideate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl N-cyanoethanimideate(1558-82-3)
• EPA Substance Registry System: Ethyl N-cyanoethanimideate(1558-82-3)

Safety Data

• Hazardous Substances Data: 1558-82-3(Hazardous Substances Data)

Usage

Preparation

To a flask equipped as in Preparation 2-6 is added 162.0 gm (1.0 mole) of ethyl orthoacetate, 42.0 gm (1.0 mole) of cyanamide, and 134.0 gm (2.0 moles) of acetic anhydride. The reaction mixture is heated to 130-140°C and the ethyl acetate and acetic acid are distilled over. The heat is removed until the initial vigorous reaction subsides and then the heat-ing is continued at 135-140°C until most of the remaining ethyl acetate and acetid acid have distilled over (approx. 1 hr). The residue is then distilled under reduced pressure to afford 100.8 gm (90%), b.p. 90-95°C (20 mm Hg).

InChI:InChI=1/C5H8N2O/c1-3-8-5(2)7-4-6/h3H2,1-2H3/b7-5-

Synthetic route

CYANAMID (420-04-2) + ethyl acetimidate hydrochloride (2208-07-3) → ethyl N‐cyanoethanimidate (1558-82-3)

Conditions	Yield
With disodium hydrogenphosphate In water at 40℃; for 4h;	95.3%
With disodium hydrogenphosphate

CYANAMID (420-04-2) + Triethyl orthoacetate (78-39-7) → ethyl N‐cyanoethanimidate (1558-82-3)

Conditions	Yield
With acetic acid for 6h; Reflux;	78%
With acetic anhydride	58%
With acetic anhydride at 100 - 140℃;	30%
With acetic anhydride at 135 - 150℃;
In acetonitrile at 20℃; for 39h; Reflux;

CYANAMID (420-04-2) + ethyl acetate (141-78-6) → ethyl N‐cyanoethanimidate (1558-82-3)

Conditions	Yield
With acetic acid for 6h; Reflux;	78%

ethyl N‐cyanoethanimidate (1558-82-3) + 1-(6-chloropyridin-3-yl)-N-methylmethanamine (120739-62-0) → acetamiprid

Conditions	Yield
at 75℃; for 9h; Industrial scale;	96%

ethyl 2-cyanoacetate (105-56-6) + ethyl N‐cyanoethanimidate (1558-82-3) → ethyl 2-cyano-3-(cyanoamino)crotonate sodium salt

Conditions	Yield
With sodium In ethanol Ambient temperature;	87%

ethyl N‐cyanoethanimidate (1558-82-3) + 3-hydrazinylpropanenitrile (353-07-1) → C6H9N5 (1072106-44-5)

Conditions	Yield
In methanol for 20h; Reflux;	86%

phosphorohydrazidic acid diethyl ester (56183-69-8) + ethyl N‐cyanoethanimidate (1558-82-3) → 5-amino-3-methyl[1,2,4]triazol-1-ylphosphonic acid diethyl ester

Conditions	Yield
With toluene-4-sulfonic acid Reflux;	81%

1,2-diamino-benzene (95-54-5) + ethyl N‐cyanoethanimidate (1558-82-3) → 2-Methyl-1H-benzimidazole (615-15-6)

Conditions	Yield
In methanol for 10h; Reflux;	79%

1H-benzimidazol-2-amine (934-32-7) + ethyl N‐cyanoethanimidate (1558-82-3) → 4-Amino-2-methylbenzimidazole<1,2-a><1,3,5>triazine (76278-99-4)

Conditions	Yield
In 1,2-dimethoxyethane Heating;	73%

4,5-dimethyl-1,2-phenylenediamine (3171-45-7) + ethyl N‐cyanoethanimidate (1558-82-3) → 2,5,6-trimethylbenzimidazole (3363-56-2)

Conditions	Yield
In methanol for 10h; Reflux;	69%

monohydrazido thiophosphoric acid diphenylester (53144-23-3) + ethyl N‐cyanoethanimidate (1558-82-3) → 5-amino-3-methyl[1,2,4]triazol-1-ylthiophosphonic acid diphenyl ester

Conditions	Yield
With toluene-4-sulfonic acid Reflux;	68%

S,S-tetramethylenesulfoximide (50578-18-2) + ethyl N‐cyanoethanimidate (1558-82-3) → C7H11N3OS (114113-46-1)

Conditions	Yield
at 80℃; for 18h;	65%

ethyl N‐cyanoethanimidate (1558-82-3) + 3-hydrazinylpropanenitrile (353-07-1) → C6H9N5 (1072106-47-8)

Conditions	Yield
In toluene for 48h; Reflux;	64%

1-Methyl-5-(4-methylphenyl)-1λ4,4-thiazin-3-amin-1-oxid (102423-32-5) + ethyl N‐cyanoethanimidate (1558-82-3) → N-Cyan-N'-(1-methyl-5-p-tolyl-1λ4,4-thiazin-3-yl)acetamidin-S-oxid (107325-92-8)

Conditions	Yield
at 150℃; for 0.25h;	61%

5-aminotetrazole (4418-61-5) + ethyl N‐cyanoethanimidate (1558-82-3) → 4-Azido-6-methyl-[1,3,5]triazin-2-ylamine

Conditions	Yield
With triethylamine In pyridine for 264h; Ambient temperature;	60%

S-benzyl-S-ethyl-sulfodiimide (30223-23-5) + ethyl N‐cyanoethanimidate (1558-82-3) → N1-(Benzylethylimino-λ6-sulfanyliden)-N2-cyanacetamidin (111268-17-8)

Conditions	Yield
at 60℃;	57%

1-Methyl-5-phenyl-1λ4,4-thiazin-3-amin-1-oxid (102423-30-3) + ethyl N‐cyanoethanimidate (1558-82-3) → N-Cyan-N'-(1-methyl-5-phenyl-1λ4,4-thiazin-3-yl)acetamidin-S-oxid (107325-91-7)

Conditions	Yield
at 150℃; for 0.25h;	57%

Methyl thioglycolate (2365-48-2) + ethyl N‐cyanoethanimidate (1558-82-3) → 4-amino-2-methyl-thiazole-5-carboxylic acid methyl ester

Conditions	Yield
With sodium hydride In tetrahydrofuran at 20℃; for 12h; Condensation;	57%

4-amino-1H-imidazole (4919-03-3) + ethyl N‐cyanoethanimidate (1558-82-3) → N-cyano-N'-(imidazol-4-yl)acetamidine (145837-48-5)

Conditions	Yield
In 1,4-dioxane	54%

tetrahydrothiophene-S,S-diimine (53245-06-0) + ethyl N‐cyanoethanimidate (1558-82-3) → N2-Cyan-N1-(tetrahydro-1-imino-λ6-thiophen-1-yliden)acetamidin (111268-15-6)

Conditions	Yield
at 60℃;	54%

ethyl 2-sulfanylacetate (623-51-8) + ethyl N‐cyanoethanimidate (1558-82-3) → 4-amino-2-methyl-thiazole-5-carboxylic acid ethyl ester

Conditions	Yield
With sodium hydride In tetrahydrofuran at 20℃; for 12h; Condensation;	53%

dimethylsulfoximine (1520-31-6) + ethyl N‐cyanoethanimidate (1558-82-3) → C5H9N3OS (114113-54-1)

Conditions	Yield
at 80℃; for 18h;	50%

dimethylsulfoxonium methylide (70775-39-2, 5367-24-8) + ethyl N‐cyanoethanimidate (1558-82-3) → <2-(Dimethyloxo-λ6-sulfanyliden)-1-methylethyliden>cyanamid (102423-28-9)

Conditions	Yield
In dimethyl sulfoxide for 24h; Ambient temperature;	46%

S-benzyl-S-methyl-sulfodiimine (30223-22-4) + ethyl N‐cyanoethanimidate (1558-82-3) → N1-(Benzyliminomethyl-λ6-sulfanyliden)-N2-cyanacetamidin (111268-16-7)

Conditions	Yield
at 60℃;	43%

(7S,8S)-8-Amino-7-hydroxy-6,6-dimethyl-5-oxo-5,6,7,8-tetrahydro-naphthalene-2-carbonitrile + ethyl N‐cyanoethanimidate (1558-82-3) → trans-4-<(N-cyanoacetimidoyl)amino>-2,2-dimethyl-3-hydroxy-1-oxo-1,2,3,4-tetrahydronaphthalene-6-carbonitrile

Conditions	Yield
at 100℃;	40%

(2-methoxyethyl)hydrazine (3044-15-3) + ethyl N‐cyanoethanimidate (1558-82-3) → C6H12N4O

Conditions	Yield
With triethylamine In ethanol at 0 - 20℃; for 18h;	39%

5-amino-2-(cyclopropanecarbonylamino)-N-(cyclopropylmethyl)-4,5,6,7-tetrahydrobenzothiophene-3-carboxamide hydrochloride + ethyl N‐cyanoethanimidate (1558-82-3) → 5-[[N-cyano-C-methyl-carbonimidoyl]amino]-2-(cyclopropanecarbonylamino)-N-(cyclopropylmethyl)-4,5,6,7-tetrahydrobenzothiophene-3-carboxamide

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In ethanol at 100℃; for 4h; Microwave irradiation;	37%

S,S-dibenzylsulphurdi-imide (30223-27-9) + ethyl N‐cyanoethanimidate (1558-82-3) → N2-Cyan-N1-(dibenzylimino-λ6-sulfanyliden)acetamidin (111268-18-9)

Conditions	Yield
at 60℃;	19%

2-Isopropyl-1-methyl-1H-imidazol-4-ylamine + ethyl N‐cyanoethanimidate (1558-82-3) → N-cyano-N'-(2-isopropyl-1-methylimidazol-4-yl)acetamidine (145837-47-4)

Conditions	Yield
In 1,4-dioxane for 1h;	16%

Upstream product

• 420-04-2 CYANAMID 
• 2208-07-3 ethyl acetimidate hydrochloride 
• 78-39-7 Triethyl orthoacetate 
• 64-17-5 ethanol 
• 75-05-8 acetonitrile 
• 1000-84-6 O-ethyl acetimidate 
• 141-78-6 ethyl acetate 

Downstream Products

• 111268-16-7 N¹-(Benzyliminomethyl-λ⁶-sulfanyliden)-N²-cyanacetamidin 
• 111268-17-8 N¹-(Benzylethylimino-λ⁶-sulfanyliden)-N²-cyanacetamidin 
• 111268-18-9 N²-Cyan-N¹-(dibenzylimino-λ⁶-sulfanyliden)acetamidin 
• 107325-91-7 N-Cyan-N'-(1-methyl-5-phenyl-1λ⁴,4-thiazin-3-yl)acetamidin-S-oxid 
• 107325-92-8 N-Cyan-N'-(1-methyl-5-p-tolyl-1λ⁴,4-thiazin-3-yl)acetamidin-S-oxid 
• 3363-56-2 2,5,6-trimethylbenzimidazole 
• 534-26-9 lysidine 
• 615-15-6 2-Methyl-1H-benzimidazole 
• 1072106-44-5 C₆H₉N₅ 
• 135410-20-7 acetamiprid 
• 339363-03-0 N'-cyano-N-(cyanomethyl)-N-methylacetimidamide 
• 51108-32-8 1,3-Dimethyl-5-amino-1,2,4-triazol 
• 129147-66-6 (4-Amino-2-methyl-benzo[4,5]imidazo[1,2-a][1,3,5]triazin-7-yl)-phenyl-methanone 

Relevant articles and documents

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Preparation method of acetamiprid

The invention relates to a preparation method of acetamiprid. The preparation method comprises the following steps of enabling 2-chloro-5-chloromethylpyridine and a methylamine water solution to be reacted so as to synthesize N- (6-chloro-3-pyridylmethyl) methylamine; enabling acetonitrile, ethanol and cyanamide to be reacted so as to synthesize ethyl N-cyanoethanimideate; and further synthesizing the acetamiprid from the N-(6-chloro-3-pyridylmethyl) methylamine and the ethyl N-cyanoethanimideate. The preparation method of the acetamiprid, disclosed by the invention, has the following advantages that through control of reaction conditions, the conversion rate of used raw materials is increased, and the preparation method is suitable for industrial production. In addition, the acetamiprid product prepared by the preparation method is high in purity, low in impurity content, and high in mole yield, and a favorable economic benefit is obtained.

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