1-[(4-methoxyphenyl)sulfonyl]-1H-pyrrole

Base Information

• Chemical Name: 1-[(4-methoxyphenyl)sulfonyl]-1H-pyrrole
• CAS No.: 18836-84-5
• Molecular Formula: C₁₁H₁₁NO₃S
• Molecular Weight: 237.279
• DSSTox Substance ID: DTXSID001332503
• Nikkaji Number: J2.457.913A
• ChEMBL ID: CHEMBL504254
• Mol file: 18836-84-5.mol

Synonyms:1-[(4-methoxyphenyl)sulfonyl]-1H-pyrrole;CHEMBL504254;CBMicro_031663;1-(4-methoxyphenyl)sulfonylpyrrole;1-(4-methoxyphenylsulfonyl)-1H-pyrrole;Cambridge id 6131840;18836-84-5;MLS001180630;DTXSID001332503;HMS2785D14;BDBM50266657;STK440979;AKOS003270406;SMR000476774;BIM-0031533.P001;SR-01000228632;SR-01000228632-1

Chemical Property of 1-[(4-methoxyphenyl)sulfonyl]-1H-pyrrole

Chemical Property:

• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 237.04596439
• Heavy Atom Count: 16
• Complexity: 309

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)S(=O)(=O)N2C=CC=C2

Technology Process of 1-[(4-methoxyphenyl)sulfonyl]-1H-pyrrole

There total 4 articles about 1-[(4-methoxyphenyl)sulfonyl]-1H-pyrrole 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: 91.0%

N-allyl-4-methoxybenzenesulfonamide (34954-40-0) + crotonaldehyde (123-73-9,4170-30-3) → 1-[(4-methoxyphenyl)sulfonyl]-1H-pyrrole (18836-84-5)

Guidance literature:

N-allyl-4-methoxybenzenesulfonamide; crotonaldehyde; With triphenylborane; In toluene; for 0.0833333h; Inert atmosphere;

With Hoveyda-Grubbs catalyst second generation; In toluene; for 0.5h; Inert atmosphere; Reflux;

DOI:10.1055/s-0030-1259083

Reference yield:

pyrrole (109-97-7,30604-81-0) + 4-methoxy-phenyl-sulphonyl chloride (98-68-0) → 1-[(4-methoxyphenyl)sulfonyl]-1H-pyrrole (18836-84-5)

Guidance literature:

With sodium hydroxide; In dichloromethane; at 0 - 20 ℃; for 17.5h; Inert atmosphere;

DOI:10.1021/ol402559z

Reference yield:

4-methoxy-phenyl-sulphonyl chloride (98-68-0) → 1-[(4-methoxyphenyl)sulfonyl]-1H-pyrrole (18836-84-5) + 1-((4-methoxyphenyl)sulfonyl)-2,5-dihydro-1H-pyrrole

Guidance literature:

Multi-step reaction with 2 steps

1.1: triethylamine / dichloromethane / 0.5 h / 0 °C

1.2: 20 °C

2.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; copper(II) bis(trifluoromethanesulfonate); oxygen / toluene / 24 h / 110 °C / 760.05 Torr / Schlenk technique

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; oxygen; copper(II) bis(trifluoromethanesulfonate); triethylamine; In dichloromethane; toluene;

DOI:10.1055/s-0039-1690002

upstream raw materials:

N-allyl-4-methoxybenzenesulfonamide

crotonaldehyde

pyrrole

4-methoxy-phenyl-sulphonyl chloride

Downstream raw materials:

p-anisyl methyl sulfone