2-(1-Benzylindol-5-YL)-N-methylethenesulfonamide

Base Information

• Chemical Name: 2-(1-Benzylindol-5-YL)-N-methylethenesulfonamide
• CAS No.: 894351-84-9
• Molecular Formula: C18H18 N2 O2 S
• Molecular Weight: 326.419
• DSSTox Substance ID: DTXSID10697586
• Mol file: 894351-84-9.mol

Synonyms:2-(1-BENZYLINDOL-5-YL)-N-METHYLETHENESULFONAMIDE;2-(1-Benzyl-1H-indol-5-yl)-N-methylethene-1-sulfonamide;DTXSID10697586;AKOS030243006;FT-0671938

Chemical Property of 2-(1-Benzylindol-5-YL)-N-methylethenesulfonamide

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 1120C
• Refractive Index: 1.612
• Boiling Point: 549.577°C at 760 mmHg
• PKA: 10.63±0.40(Predicted)
• Flash Point: 286.174°C
• PSA: 59.48000
• Density: 1.201g/cm³
• LogP: 4.68120
• Storage Temp.: Room Temperature
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 326.10889899
• Heavy Atom Count: 23
• Complexity: 506

Purity/Quality:

97% ^*data from raw suppliers

(1E)-N-METHYL-2-[1-(PHENYL METHYL)-1H-INDOL-5-YL]ETHENE SULFONAMIDE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CNS(=O)(=O)C=CC1=CC2=C(C=C1)N(C=C2)CC3=CC=CC=C3
• Uses: Intermediate for the preparation of Naratriptan and other indole sulfonamide derivatives.

Technology Process of 2-(1-Benzylindol-5-YL)-N-methylethenesulfonamide

There total 2 articles about 2-(1-Benzylindol-5-YL)-N-methylethenesulfonamide 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: 73.0%

N-tert-butoxycarbonyl(methanesulfonyl)methylamine (894351-83-8) + 1-benzyl-1H-indole-5-carbaldehyde (63263-88-7) → 2-(1-benzyl-1H-indol-5-yl)ethenesulfonic acid methylamide (894351-84-9)

Guidance literature:

N-tert-butoxycarbonyl(methanesulfonyl)methylamine; With potassium tert-butylate; In tetrahydrofuran; at -78 ℃; for 1h;

1-benzyl-1H-indole-5-carbaldehyde; In tetrahydrofuran; at -78 - 0 ℃;

DOI:10.3987/COM-06-10670

Reference yield:

N-benzylindoline-5-carboxaldehyde (63263-84-3) → 2-(1-benzyl-1H-indol-5-yl)ethenesulfonic acid methylamide (894351-84-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 75 percent / DDQ / CH₂Cl₂ / 3 h / 0 °C

2.1: t-BuOK / tetrahydrofuran / 1 h / -78 °C

2.2: 73 percent / tetrahydrofuran / -78 - 0 °C

With potassium tert-butylate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane;

DOI:10.3987/COM-06-10670

Reference yield: 84.0%

2-(1-benzyl-1H-indol-5-yl)ethenesulfonic acid methylamide (894351-84-9) → 2-(1-benzyl-1H-indol-5-yl)ethanesulfonic acid methylamide (894351-85-0)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; at 20 ℃; for 2h; under 3750.3 Torr;

DOI:10.3987/COM-06-10670

upstream raw materials:

N-tert-butoxycarbonyl(methanesulfonyl)methylamine

1-benzyl-1H-indole-5-carbaldehyde

N-benzylindoline-5-carboxaldehyde

Downstream raw materials:

2-(1-benzyl-1H-indol-5-yl)ethanesulfonic acid methylamide

2-[1-benzyl-3-(1-methyl-1,2,3,6-tetrahydro-pyridin-4-yl)-1H-indol-5-yl]-ethanesulfonic acid methylamide

N-methyl-2-[1-benzyl-3-(1-methylpiperidin-4-yl)-1H-indol-5-yl]ethanesulfonamide

naratriptan