Benzamide, 2-iodo-N-2-propenyl-N-[(trimethylsilyl)ethynyl]-

Base Information

• Chemical Name: Benzamide, 2-iodo-N-2-propenyl-N-[(trimethylsilyl)ethynyl]-
• CAS No.: 646029-27-8
• Molecular Formula: C15H18INOSi
• Molecular Weight: 383.304
• DSSTox Substance ID: DTXSID50461086
• Nikkaji Number: J2.002.218C
• Wikidata: Q82285334
• Mol file: 646029-27-8.mol

Synonyms:646029-27-8;Benzamide, 2-iodo-N-2-propenyl-N-[(trimethylsilyl)ethynyl]-;DTXSID50461086

Chemical Property of Benzamide, 2-iodo-N-2-propenyl-N-[(trimethylsilyl)ethynyl]-

Chemical Property:

• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 5
• Exact Mass: 383.02024
• Heavy Atom Count: 19
• Complexity: 401

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[Si](C)(C)C#CN(CC=C)C(=O)C1=CC=CC=C1I

Technology Process of Benzamide, 2-iodo-N-2-propenyl-N-[(trimethylsilyl)ethynyl]-

There total 2 articles about Benzamide, 2-iodo-N-2-propenyl-N-[(trimethylsilyl)ethynyl]- 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: 63.0%

2-iodo-N-(2-propen-1-yl)benzamide (66896-70-6) + (2-(trimethylsilyl)ethynyl)(phenyl)iodonium trifluoromethanesulfonate → N-allyl-2-iodo-N-((trimethylsilanyl)ethynyl)benzamide (646029-27-8)

Guidance literature:

With potassium hexamethylsilazane; In toluene; at 20 ℃;

DOI:10.1021/ol049302m

Reference yield:

2-Iodobenzoic acid (88-67-5) → N-allyl-2-iodo-N-((trimethylsilanyl)ethynyl)benzamide (646029-27-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 73 percent / N-ethyl-N'-(3-(dimethylaminio)propyl)carbodiimide*HCl; DMAP / CH₂Cl₂; tetrahydrofuran / 12 h / 0 - 20 °C

2: 63 percent / KHMDS / toluene / 24 h / 20 °C

With dmap; potassium hexamethylsilazane; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1016/j.tet.2005.11.089

Reference yield: 85.0%

N-allyl-2-iodo-N-((trimethylsilanyl)ethynyl)benzamide (646029-27-8) → N-allyl-N-ethynyl-2-iodo-benzamide (646029-28-9)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃;

DOI:10.1021/ol049302m

upstream raw materials:

2-iodo-N-(2-propen-1-yl)benzamide

2-Iodobenzoic acid

Downstream raw materials:

N-allyl-N-ethynyl-2-iodo-benzamide

N-allyl-2-iodo-N-(prop-1-ynyl)benzamide

[N-allyl-N-(2-iodobenzoyl)amino]propynoic acid ethyl ester