3-Hydroxy-1-(toluene-4-sulfonyl)-1H-pyridin-2-one

Base Information

• Chemical Name: 3-Hydroxy-1-(toluene-4-sulfonyl)-1H-pyridin-2-one
• CAS No.: 316354-21-9
• Molecular Formula: C12H11NO4S
• Molecular Weight: 265.29
• DSSTox Substance ID: DTXSID80460981
• Nikkaji Number: J1.412.031I
• Wikidata: Q82285187
• Mol file: 316354-21-9.mol

Synonyms:3-Hydroxy-1-(toluene-4-sulfonyl)-1H-pyridin-2-one;316354-21-9;SCHEMBL1770928;DTXSID80460981;WCEPQPZGFHITGY-UHFFFAOYSA-N;1-(4'-Methylbenzenesulfonyl)-3-hydroxypyridin-2(1H)-one

Chemical Property of 3-Hydroxy-1-(toluene-4-sulfonyl)-1H-pyridin-2-one

Chemical Property:

• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 265.04087901
• Heavy Atom Count: 18
• Complexity: 493

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)N2C=CC=C(C2=O)O

Technology Process of 3-Hydroxy-1-(toluene-4-sulfonyl)-1H-pyridin-2-one

There total 6 articles about 3-Hydroxy-1-(toluene-4-sulfonyl)-1H-pyridin-2-one 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: 98.0%

3-[(tert-butyl)dimethylsilyloxy]-1-[(4-methylphenyl)sulfonyl]-1H-pyridin-2-one (141667-31-4) → 3-hydroxy-1-[(4-methylphenyl)sulfonyl]-1H-pyridin-2-one (316354-21-9)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 23 ℃; for 24h;

DOI:10.1002/hlca.200390320

Reference yield:

3-<(tert-butyldimethylsilyl)oxy>-2-pyridone (141667-58-5) + p-toluenesulfonyl chloride (98-59-9) → 3-hydroxy-1-[(4-methylphenyl)sulfonyl]-1H-pyridin-2-one (316354-21-9)

Guidance literature:

3-<(tert-butyldimethylsilyl)oxy>-2-pyridone; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.333333h;

p-toluenesulfonyl chloride; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 1h;

Reference yield:

3-<(tert-butyldimethylsilyl)oxy>-2-pyridone (141667-58-5) → 3-hydroxy-1-[(4-methylphenyl)sulfonyl]-1H-pyridin-2-one (316354-21-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: MeLi / diethyl ether / 2 h / 0 °C

1.2: 82 percent / diethyl ether / 30 h / 23 °C

2.1: 98 percent / BF₃*OEt₂ / CH₂Cl₂ / 24 h / 23 °C

With boron trifluoride diethyl etherate; methyllithium; In diethyl ether; dichloromethane;

DOI:10.1002/hlca.200390320

upstream raw materials:

3-[(tert-butyl)dimethylsilyloxy]-1-[(4-methylphenyl)sulfonyl]-1H-pyridin-2-one

dihydroxypyridine

3-<(tert-butyldimethylsilyl)oxy>-2-pyridone

p-toluenesulfonyl chloride

Downstream raw materials:

1-(4% Methylbenzenesulfonyl)-3-hydroxy-4-(pyrrolidin-1-ylmethyl)pyridin-2(1H)-one