(E)-3-(4-chlorophenyl)-4-cyano-N-((dimethylamino)methylene)-5-(morpholin-4-yl)thiophene-2-carboxamide

Base Information

• Chemical Name: (E)-3-(4-chlorophenyl)-4-cyano-N-((dimethylamino)methylene)-5-(morpholin-4-yl)thiophene-2-carboxamide
• CAS No.: 1335330-84-1
• Molecular Formula: C₁₉H₁₉ClN₄O₂S
• Molecular Weight: 402.904
• Mol file: 1335330-84-1.mol

Synonyms:(E)-3-(4-chlorophenyl)-4-cyano-N-((dimethylamino)methylene)-5-(morpholin-4-yl)thiophene-2-carboxamide

Chemical Property of (E)-3-(4-chlorophenyl)-4-cyano-N-((dimethylamino)methylene)-5-(morpholin-4-yl)thiophene-2-carboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-3-(4-chlorophenyl)-4-cyano-N-((dimethylamino)methylene)-5-(morpholin-4-yl)thiophene-2-carboxamide

There total 7 articles about (E)-3-(4-chlorophenyl)-4-cyano-N-((dimethylamino)methylene)-5-(morpholin-4-yl)thiophene-2-carboxamide 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: 90.0%

3-(4-chlorophenyl)-4-cyano-5-(morpholin-4-yl)thiophene-2-carboxamide (1335330-78-3) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → (E)-3-(4-chlorophenyl)-4-cyano-N-((dimethylamino)methylene)-5-(morpholin-4-yl)thiophene-2-carboxamide (1335330-84-1)

Guidance literature:

at 110 ℃; for 1.5h;

DOI:10.1021/ml200126j

Reference yield:

4-cyano-3-iodo-5-(methylthio)thiophene-2-carboxylic acid ethyl ester → (E)-3-(4-chlorophenyl)-4-cyano-N-((dimethylamino)methylene)-5-(morpholin-4-yl)thiophene-2-carboxamide (1335330-84-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 - 20 °C

1.2: 16 h / 20 °C

2.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / DCE; ethanol / 16 h / Inert atmosphere; Reflux

3.1: water; sodium hydroxide / tetrahydrofuran; ethanol / 20 °C

3.2: pH 6

4.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 3 h / 20 °C / Inert atmosphere

5.1: ammonia / diethyl ether

6.1: 1.5 h / 110 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; oxalyl dichloride; ammonia; water; potassium carbonate; N,N-dimethyl-formamide; 3-chloro-benzenecarboperoxoic acid; sodium hydroxide; In tetrahydrofuran; DCE; diethyl ether; ethanol; dichloromethane; 2.1: Suzuki coupling;

DOI:10.1021/ml200126j

Reference yield:

C16H12Cl2N2O2S → (E)-3-(4-chlorophenyl)-4-cyano-N-((dimethylamino)methylene)-5-(morpholin-4-yl)thiophene-2-carboxamide (1335330-84-1)

Guidance literature:

Multi-step reaction with 2 steps

1: ammonia / diethyl ether

2: 1.5 h / 110 °C

With ammonia; In diethyl ether;

DOI:10.1021/ml200126j

upstream raw materials:

4-cyano-3-iodo-5-(morpholin-4-yl)thiophene-2-carboxylic acid ethyl ester

3-(4-chlorophenyl)-4-cyano-5-(morpholin-4-yl)thiophene-2-carboxylic acid

ethyl 3-(4-chlorophenyl)-4-cyano-5-(morpholin-4-yl)thiophene-2-carboxylate

3-(4-chlorophenyl)-4-cyano-5-(morpholin-4-yl)thiophene-2-carboxamide

Downstream raw materials:

4-(4-chlorophenyl)-2-(morpholin-4-yl)-5-(1H-1,2,4-triazol-3-yl)thiophene-3-carbonitrile