2-(2-Oxoindolin-4-yl)ethyl 4-methylbenzenesulfonate

Base Information

• Chemical Name: 2-(2-Oxoindolin-4-yl)ethyl 4-methylbenzenesulfonate
• CAS No.: 139122-20-6
• Molecular Formula: C17H17NO4S
• Molecular Weight: 331.392
• Hs Code.: 2933790090
• European Community (EC) Number: 604-111-0
• DSSTox Substance ID: DTXSID60435096
• Wikidata: Q72495314
• Mol file: 139122-20-6.mol

Synonyms:139122-20-6;2-(2-Oxoindolin-4-yl)ethyl 4-methylbenzenesulfonate;4-[2-[[(4-METHYLPHENYL)SULFONYL]OXY]ETHYL]-2-OXOINDOLE;4-[2-[[(4-Methylphenyl)sulfonyl]oxy]ethyl]-1,3-dihydroindol-2-one;4-[2-[[(4-Methylphenyl)sulfonyl]oxy]ethyl]-1,3-dihydro-2H-indole-2-one;2-(2-OXO-1,3-DIHYDROINDOL-4-YL)ETHYL 4-METHYLBENZENESULFONATE;2H-Indol-2-one, 1,3-dihydro-4-[2-[[(4-methylphenyl)sulfonyl]oxy]ethyl]-;4-[2'-[[(4-methylphenyl)sulfonyl]oxy]ethyl]-1,3-dihydro-2h-indole-2-one;2-(2-Oxoindolin-4-yl)ethyl4-methylbenzenesulfonate;SCHEMBL5842590;DTXSID60435096;OGFUVAXFYGBCAK-UHFFFAOYSA-N;MFCD09952011;AKOS005258767;SB64173;AS-17438;FT-0658533;A807487;J-007236;J-514231;2-(2-Oxo-2,3-dihydro-1H-indol-4-yl)ethyl 4-methylbenzene-1-sulfonate

Chemical Property of 2-(2-Oxoindolin-4-yl)ethyl 4-methylbenzenesulfonate

Chemical Property:

• Boiling Point: 561.181 °C at 760 mmHg
• PKA: 14.02±0.20(Predicted)
• Flash Point: 293.192 °C
• PSA: 80.85000
• Density: 1.312 g/cm³
• LogP: 3.65640
• Storage Temp.: 2-8°C
• Solubility.: Chloroform, Methanol
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 331.08782920
• Heavy Atom Count: 23
• Complexity: 519

Purity/Quality:

99% ^*data from raw suppliers

4-[2-[[(4-Methylphenyl)sulfonyl]oxy]ethyl]-1,3-dihydroindol-2-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)OCCC2=C3CC(=O)NC3=CC=C2

Technology Process of 2-(2-Oxoindolin-4-yl)ethyl 4-methylbenzenesulfonate

There total 27 articles about 2-(2-Oxoindolin-4-yl)ethyl 4-methylbenzenesulfonate 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: 87.0%

p-toluenesulfonyl chloride (98-59-9) + 4-(2'-hydroxyethyl)-1,3-dihydro-2H-indol-2-one (139122-19-3) → 2-(2-oxo-2,3-dihydro-1H-indol-4-yl)ethyl-4-methylbenzene-1-sulfonate (139122-20-6)

Guidance literature:

With pyridine; In dichloromethane; at 5 - 10 ℃; for 4h;

DOI:10.1002/jhet.5570320334

Reference yield:

2-(2-bromoethyl)benzaldehyde (22901-09-3) → 2-(2-oxo-2,3-dihydro-1H-indol-4-yl)ethyl-4-methylbenzene-1-sulfonate (139122-20-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 80 percent / MeONa / methanol / 1 h / 0 °C

2: 53 percent / AcCl, FeCl₃ / CH₂Cl₂ / 3 h / 0 - 5 °C

3: 95 percent / aq. NaH₂PO₂ / 10percent Pd-C / ethyl acetate / 0.58 h / Heating

4: 89 percent / ethanol; H₂O / 24 h / Heating

5: 70 percent / aq. HCl / 2.5 h / Heating

6: 87 percent / pyridine / CH₂Cl₂ / 4 h / 5 - 10 °C

With pyridine; hydrogenchloride; sodium hypophosphite; sodium methylate; iron(III) chloride; acetyl chloride; palladium on activated charcoal; In methanol; ethanol; dichloromethane; water; ethyl acetate;

DOI:10.1002/jhet.5570320334

Reference yield:

isochromane (493-05-0) → 2-(2-oxo-2,3-dihydro-1H-indol-4-yl)ethyl-4-methylbenzene-1-sulfonate (139122-20-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 100 percent / ZnCl₂ / CH₂Cl₂ / 1 h / Heating

2: 1.) hexamethylenetetramine, 2.) aq. AcOH / 1.) ethanol, reflux, 90 min, 2.) ethanol, reflux

3: 87 percent / AcOH, n-BuNH₂ / methanol / 18 h / 22 °C

4: 64 percent / AcCl, FeCl₃ / CH₂Cl₂ / 1 h / 0 - 5 °C

5: hydrazine hydrate, 10percent Pd-C / methanol; H₂O / 0.5 h / Heating

6: aq. NaOH / methanol / 0.5 h / Heating

7: 87 percent / pyridine / CH₂Cl₂ / 4 h / 5 - 10 °C

With pyridine; sodium hydroxide; palladium on activated charcoal; hexamethylenetetramine; iron(III) chloride; hydrazine hydrate; acetic acid; N-butylamine; acetyl chloride; zinc(II) chloride; In methanol; dichloromethane; water;

DOI:10.1002/jhet.5570320334

upstream raw materials:

p-toluenesulfonyl chloride

4-(2'-hydroxyethyl)-1,3-dihydro-2H-indol-2-one

isochromane

2-(2-bromoethyl)benzaldehyde

Downstream raw materials:

Ropinirole

4-ethylenyl-1,3-dihydro-2H-indol-2-one

ropinirole hydrochloride

Refernces

• 1、 -. "Method for preparing ropinirole hydrochloride". Paragraph 0062; 0063; 0064. . Retrieved 2018/09/12.
• 2、 -. "Improved preparation method for ropinirole hydrochloride". Paragraph 0051; 0052. . Retrieved 2016/10/09.