Ethyl (4,5-dicyano-1H-pyrazol-3-yl)methanimidate

Base Information

• Chemical Name: Ethyl (4,5-dicyano-1H-pyrazol-3-yl)methanimidate
• CAS No.: 84941-17-3
• Molecular Formula: C8H7N5O
• Molecular Weight: 189.176
• DSSTox Substance ID: DTXSID40515885
• Mol file: 84941-17-3.mol

Synonyms:84941-17-3;3,4-dicyano-5-ethoxymethyleneaminopyrazole;Ethyl (4,5-dicyano-1H-pyrazol-3-yl)methanimidate;DTXSID40515885

Chemical Property of Ethyl (4,5-dicyano-1H-pyrazol-3-yl)methanimidate

Chemical Property:

• XLogP3: 0.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 189.06505986
• Heavy Atom Count: 14
• Complexity: 308

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCOC=NC1=NNC(=C1C#N)C#N

Technology Process of Ethyl (4,5-dicyano-1H-pyrazol-3-yl)methanimidate

There total 2 articles about Ethyl (4,5-dicyano-1H-pyrazol-3-yl)methanimidate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 81.0%

orthoformic acid triethyl ester (122-51-0) + 5-amino-1H-pyrazole-3,4-dicarbonitrile (54385-49-8) → 3,4-Dicyano-5-ethoxymethyleneaminopyrazole (84941-17-3)

Guidance literature:

at 100 - 110 ℃; for 4h;

DOI:10.1007/BF00506622

Reference yield: 16.0%

orthoformic acid triethyl ester (122-51-0) + 5-amino-1H-pyrazole-3,4-dicarbonitrile (54385-49-8) → N2-Ethyl-3,4-dicyano-5-ethoxymethyleneaminopyrazole (84941-21-9) + N1-Ethyl-3,4-dicyano-5-ethoxymethyleneaminopyrazole (84941-18-4) + 3,4-Dicyano-5-ethoxymethyleneaminopyrazole (84941-17-3)

Guidance literature:

for 5h; Title compound not separated from byproducts; Heating;

DOI:10.1007/BF00506622

Reference yield:

3,4-Dicyano-5-ethoxymethyleneaminopyrazole (84941-17-3) → 1-(β-D-Ribofuranosyl)-3-thiocarbamoyl-4-aminopyrazolo<3,4-d>pyrimidine (55559-54-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 1) CH₃ONa; 2) H₂S / 1) MeOH; 2) reflux, 4 h

2: 89 percent / 1M aq. NaOH / H₂O / 2 h / 20 °C

3: 61 percent / Iodine / 0.75 h / 165 °C / 10 - 15 Torr

4: 53 percent / H₂S, Triethylamine / ethanol / 1.5 h / 20 °C

5: 52 percent / gaseous NH₃ / methanol / 8 h / 100 °C

With sodium hydroxide; hydrogen sulfide; ammonia; iodine; sodium methylate; triethylamine; In methanol; ethanol; water;

DOI:10.1007/BF00506295

upstream raw materials:

orthoformic acid triethyl ester

5-amino-1H-pyrazole-3,4-dicarbonitrile

Downstream raw materials:

1-(β-D-Ribofuranosyl)-3-thiocarbamoyl-4-aminopyrazolo<3,4-d>pyrimidine

Refernces

FREE-RADICAL HYDROXYMETHYLATION OF BENZIMIDAZOLE

10.1007/BF00506621

The research investigates the free-radical hydroxymethylation of benzimidazole derivatives and the condensation of 3,4-dicyano-5-aminopyrazole with ethyl orthoformate. In the hydroxymethylation study, benzimidazole derivatives such as 1-methylbenzimidazole and 1-phenylbenzimidazole were subjected to free-radical hydroxymethylation using ammonium persulfate in methanol and sulfuric acid, with silver ions as a catalyst to enhance yields. The study found that benzimidazole displayed lower activity than quinoline in the addition of the hydroxymethyl radical, and the yields of hydroxymethylation products were influenced by the ability of intermediate benzimidazolium cation radicals to undergo oxidation. In the condensation study, 3,4-dicyano-5-aminopyrazole was reacted with ethyl orthoformate under different conditions to produce compounds like N-ethyl-3,4-dicyano-5-ethoxymethyleneaminopyrazole and 3,4-dicyano-5-ethoxymethyleneaminopyrazole. The formation of these products and their subsequent conversion to pyrazolo[3,4-d]pyrimidines using a methanol solution of ammonia were also explored.