N-[2-(diethylamino)ethyl]-4-nitrobenzamide

Base Information

• Chemical Name: N-[2-(diethylamino)ethyl]-4-nitrobenzamide
• CAS No.: 1664-52-4
• Molecular Formula: C13H19 N3 O3
• Molecular Weight: 265.312
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID40168097
• Nikkaji Number: J29.498E
• Wikidata: Q83037603
• ChEMBL ID: CHEMBL3302168
• Mol file: 1664-52-4.mol

Synonyms:4-nitroprocainamide;4-nitroprocainamide hydrochloride;4-nitroprocainamide monohydrochloride

Chemical Property of N-[2-(diethylamino)ethyl]-4-nitrobenzamide

Chemical Property:

• Vapor Pressure: 7.22E-08mmHg at 25°C
• Refractive Index: 1.546
• Boiling Point: 437.9°Cat760mmHg
• Flash Point: 218.6°C
• PSA: 78.16000
• Density: g/cm³
• LogP: 2.58050
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 265.14264148
• Heavy Atom Count: 19
• Complexity: 292

Purity/Quality:

99% ^*data from raw suppliers

4-NITRO-N-(B-DIETHYLAMINOETHYL)BENZAMIDE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCN(CC)CCNC(=O)C1=CC=C(C=C1)[N+](=O)[O-]

Technology Process of N-[2-(diethylamino)ethyl]-4-nitrobenzamide

There total 10 articles about N-[2-(diethylamino)ethyl]-4-nitrobenzamide 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: 99.0%

N,N-diethylethylenediamine (100-36-7) + 4-nitro-benzoic acid (62-23-7) → N-(2-(diethylamino)ethyl)-4-nitrobenzamide (1664-52-4)

Guidance literature:

With tetramethylorthosilicate; In toluene; at 110 ℃; for 3h; Inert atmosphere;

DOI:10.1021/acs.orglett.7b03841

Reference yield: 98.0%

4-nitrobenzoic acid methyl ester (619-50-1) + N,N-diethylethylenediamine (100-36-7) → N-(2-(diethylamino)ethyl)-4-nitrobenzamide (1664-52-4)

Guidance literature:

With ammonium nitrate; In neat (no solvent); at 20 ℃; for 12h; Green chemistry;

DOI:10.1246/cl.140846

Reference yield: 88.0%

4-nitro-benzoyl chloride (122-04-3) + N,N-diethylethylenediamine (100-36-7) → N-(2-(diethylamino)ethyl)-4-nitrobenzamide (1664-52-4)

Guidance literature:

With silica gel; potassium carbonate; for 1h; Milling; Industrial scale;

DOI:10.3390/molecules23123163

upstream raw materials:

N-(2-diethylamino-ethyl)-4-nitro-benzamidine; dihydrochloride

4-nitro-benzoyl chloride

N,N-diethylethylenediamine

4-nitro-benzoic acid

Downstream raw materials:

2-(4-<2-Diethylamino-ethylcarbamoyl>-phenylcarbamoyl)-2-(4-chlor-phenoxy)-propan

4-amino-N-(2-diethylaminoethyl)benzamide

Refernces

• 1、 Boyle, Mhairi,Livingstone, Keith,Henry, Martyn C.,Elwood, Jessica M. L.,Lopez-Fernandez, J. Daniel,Jamieson, Craig. "Amide Bond Formation via the Rearrangement of Nitrile Imines Derived from N-2-Nitrophenyl Hydrazonyl Bromides". . p. 334 - 338. Retrieved 2022/01/20.
• 2、 Portada, Tomislav,Margeti?, Davor,?trukil, Vjekoslav. "Mechanochemical catalytic transfer hydrogenation of aromatic nitro derivatives". supporting information. . Retrieved 2018/12/11.