Acetamide, 2-cyano-2-diazo-

Base Information

• Chemical Name: Acetamide, 2-cyano-2-diazo-
• CAS No.: 85059-18-3
• Molecular Formula: C3H2N4O
• Molecular Weight: 110.075

Synonyms:

Chemical Property of Acetamide, 2-cyano-2-diazo-

Chemical Property:

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SDS file from LookChem

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Technology Process of Acetamide, 2-cyano-2-diazo-

There total 1 articles about Acetamide, 2-cyano-2-diazo- 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: 40.0%

5-amino-4-chloro-6-oxo-1,6-dihydropyrimidine (3137-60-8) → 2-cyano-2-diazoacetamide (85059-18-3) + 4-carbamoyl-5-chloro-1,2,3-triazole (85059-19-4)

Guidance literature:

With hydrogenchloride; sodium nitrite; In water; 1.) -5 - 0 deg C, 1.5 h, 2.) room temp.,;

Reference yield: 93.0%

2-cyano-2-diazoacetamide (85059-18-3) → 4-carbamoyl-5-amino-1,2,3-thiadiazole (85059-20-7)

Guidance literature:

With hydrogen sulfide; In ethanol; at 20 ℃; for 5h;

DOI:10.1007/BF00962685

Reference yield: 90.0%

2-cyano-2-diazoacetamide (85059-18-3) → hydrochloride of 2-cyano-2-diazoacetamide + 4-carbamoyl-5-chloro-1,2,3-triazole (85059-19-4)

Guidance literature:

With hydrogenchloride; In chloroform; for 1440h; Ambient temperature;

DOI:10.1007/BF00506405

upstream raw materials:

5-amino-4-chloro-6-oxo-1,6-dihydropyrimidine

Downstream raw materials:

Cyanglyoxalsaeureamid-triphenylphosphazin

4-carbamoyl-5-chloro-1,2,3-triazole

5-amino-1,2,3-thiadiazole-4-carbothioamide

2-Hydrazono-2-cyanoacetamide

Refernces

Heterocyclization of compounds containing diazo and cyano groups. 6. Theoretical and experimental investigations of cyclization of 2-cyano-2-diazoacetamides to 5-hydroxy-1,2,3-triazole-4-carbonitriles

10.1007/BF02256840

The research focuses on the heterocyclization of compounds containing diazo and cyano groups, specifically the cyclization of 2-cyano-2-diazoacetamides to 5-hydroxy-1,2,3-triazole-4-carbonitriles. The purpose of this study was to investigate the theoretical and experimental aspects of this cyclization process, with the aim of understanding the mechanisms involved in the transformation. The researchers synthesized a series of N-alkyl- and N-aryl-2-(cyano-2-diazoacetamides) and examined their cyclization to 5-hydroxy-1,2,3-triazoles using kinetic and theoretical methods, including the B3LYP/6-31+G* method. The study concluded that there is a difference in the mechanisms of cyclization between N-alkyl and N-aryl derivatives of 2-cyano-2-diazoacetamide; the N-alkyl derivatives cyclize via a monorotatory mechanism, while the N-aryl derivatives cyclize through a mechanism involving heteroelectrocyclization of 2-diazoacetimidates. Key chemicals used in the process include 2-amino-2-cyanoacetamides, 2-cyano-2-diazoacetamides, 5-hydroxy-1,2,3-triazole-4-carbonitriles, and their respective derivatives, along with reagents like sodium nitrite, hydrochloric acid, and sodium ethoxide.

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