(1-benzenesulfonyl-6-cyano-2,3-dihydro-1H-pyridin-4-ylidene)acetic acid ethyl ester

Base Information

• Chemical Name: (1-benzenesulfonyl-6-cyano-2,3-dihydro-1H-pyridin-4-ylidene)acetic acid ethyl ester
• CAS No.: 1314131-81-1
• Molecular Formula: C₁₆H₁₆N₂O₄S
• Molecular Weight: 332.38
• Mol file: 1314131-81-1.mol

Synonyms:(1-benzenesulfonyl-6-cyano-2,3-dihydro-1H-pyridin-4-ylidene)acetic acid ethyl ester

Chemical Property of (1-benzenesulfonyl-6-cyano-2,3-dihydro-1H-pyridin-4-ylidene)acetic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1-benzenesulfonyl-6-cyano-2,3-dihydro-1H-pyridin-4-ylidene)acetic acid ethyl ester

There total 4 articles about (1-benzenesulfonyl-6-cyano-2,3-dihydro-1H-pyridin-4-ylidene)acetic acid ethyl ester 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: 72.0%

trimethylsilyl cyanide (7677-24-9) + (1-benzenesulfonyl-2,3-dihydro-1H-pyridin-4-ylidene)acetic acid ethyl ester (1314131-79-7) → (1-benzenesulfonyl-2,3-dihydro-1H-pyridin-4-ylidene)bromoacetic acid ethyl ester (1314131-94-6) + (1-benzenesulfonyl-6-cyano-2,3-dihydro-1H-pyridin-4-ylidene)acetic acid ethyl ester (1314131-81-1)

Guidance literature:

trimethylsilyl cyanide; (1-benzenesulfonyl-2,3-dihydro-1H-pyridin-4-ylidene)acetic acid ethyl ester; With N-Bromosuccinimide; In dichloromethane; at 20 ℃; for 0.0833333h; Inert atmosphere;

With boron trifluoride diethyl etherate;

In dichloromethane; at 20 ℃; for 3h; Inert atmosphere;

DOI:10.1016/j.tet.2011.04.102

Reference yield:

1-benzenesulfonyl-piperidin-4-one (34259-86-4) → (1-benzenesulfonyl-2,3-dihydro-1H-pyridin-4-ylidene)bromoacetic acid ethyl ester (1314131-94-6) + (1-benzenesulfonyl-6-cyano-2,3-dihydro-1H-pyridin-4-ylidene)acetic acid ethyl ester (1314131-81-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: N-Bromosuccinimide; acetic acid / Inert atmosphere

2.1: methanol / tetrahydrofuran / 12 h / Reflux; Inert atmosphere

3.1: toluene-4-sulfonic acid; trimethyl orthoformate / dichloromethane / 0.33 h / 20 °C / Inert atmosphere

3.2: 22 h / Inert atmosphere; Reflux

4.1: N-Bromosuccinimide / dichloromethane / 0.08 h / 20 °C / Inert atmosphere

4.3: 3 h / 20 °C / Inert atmosphere

With methanol; N-Bromosuccinimide; toluene-4-sulfonic acid; acetic acid; trimethyl orthoformate; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.tet.2011.04.102

Reference yield:

1-benzenesulfonyl-3-bromopiperidine-4-one (919491-04-6) → (1-benzenesulfonyl-2,3-dihydro-1H-pyridin-4-ylidene)bromoacetic acid ethyl ester (1314131-94-6) + (1-benzenesulfonyl-6-cyano-2,3-dihydro-1H-pyridin-4-ylidene)acetic acid ethyl ester (1314131-81-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: methanol / tetrahydrofuran / 12 h / Reflux; Inert atmosphere

2.1: toluene-4-sulfonic acid; trimethyl orthoformate / dichloromethane / 0.33 h / 20 °C / Inert atmosphere

2.2: 22 h / Inert atmosphere; Reflux

3.1: N-Bromosuccinimide / dichloromethane / 0.08 h / 20 °C / Inert atmosphere

3.3: 3 h / 20 °C / Inert atmosphere

With methanol; N-Bromosuccinimide; toluene-4-sulfonic acid; trimethyl orthoformate; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.tet.2011.04.102

upstream raw materials:

1-benzenesulfonyl-3-bromopiperidine-4-one

trimethylsilyl cyanide

(1-benzenesulfonyl-2,3-dihydro-1H-pyridin-4-ylidene)acetic acid ethyl ester

1-benzenesulfonyl-4,4-dimethoxy-piperidin-3-ol

Downstream raw materials:

(1-benzenesulfonyl-6-cyano-1,2,3,4-tetrahydropyridin-4-yl)acetic acid ethyl ester