N-(1,3-dioxoisoindol-2-yl)benzamide

Base Information

• Chemical Name: N-(1,3-dioxoisoindol-2-yl)benzamide
• CAS No.: 16067-65-5
• Molecular Formula: C15H10N2O3
• Molecular Weight: 266.256
• DSSTox Substance ID: DTXSID50351099
• Nikkaji Number: J929.236E
• Wikidata: Q82127239
• Mol file: 16067-65-5.mol

Synonyms:16067-65-5;N-(1,3-Dioxoisoindolin-2-yl)benzamide;N-(1,3-dioxoisoindol-2-yl)benzamide;N-phthalimidobenzamide;TimTec1_000761;SCHEMBL11817094;DTXSID50351099;QDRKIFVTZFDQDJ-UHFFFAOYSA-N;HMS1536C13;STK391551;AKOS000422174;NCGC00175148-01;BRD-K29624569-001-01-0;N-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)benzamide;N-(1,3-DIOXO-1,3-DIHYDRO-ISOINDOL-2-YL)-BENZAMIDE

Chemical Property of N-(1,3-dioxoisoindol-2-yl)benzamide

Chemical Property:

• Melting Point: 218 °C
• PSA: 69.97000
• Density: 1.43±0.1 g/cm3(Predicted)
• LogP: 2.14030
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 266.06914219
• Heavy Atom Count: 20
• Complexity: 405

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(=O)NN2C(=O)C3=CC=CC=C3C2=O

Technology Process of N-(1,3-dioxoisoindol-2-yl)benzamide

There total 13 articles about N-(1,3-dioxoisoindol-2-yl)benzamide 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: 96.0%

phthalic anhydride (85-44-9) + benzoic acid hydrazide (613-94-5) → N-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-benzamide (16067-65-5)

Guidance literature:

In toluene; for 3h; Heating;

DOI:10.1002/ejoc.200300445

Reference yield: 57.0%

phthalic anhydride (85-44-9) + Benzylhydrazine (555-96-4) → N-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-benzamide (16067-65-5)

Guidance literature:

With acetic acid; at 120 ℃; for 2h; Inert atmosphere;

DOI:10.1016/j.ejmech.2014.06.006

Reference yield:

phthalic anhydride (85-44-9) → N-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-benzamide (16067-65-5)

Guidance literature:

Multi-step reaction with 3 steps

1: tetrahydrofuran / 0.08 h / 20 °C

2: 1,3-dicyclohexylcarbodiimide / tetrahydrofuran / 1 h

3: acetic acid; triethylamine / tetrahydrofuran / 1 h / Heating

With acetic acid; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; 1: Acylation / 2: Cyclization / 3: Isomerization;

DOI:10.1021/jo000225s

upstream raw materials:

phthalic anhydride

benzoic acid hydrazide

N-aminophthalamide

benzoyl chloride

Downstream raw materials:

N-benzyl-N-benzoylaminophthalimide

N-methyl-N-benzoylaminophthalimide

1-benzyl-1-benzoylhydrazine

N'-benzoyl-N'-benzyl-N-[2-(pyrrolidine-1-carbonyl)-benzoyl]-hydrazinecarboxylic acid tert-butyl ester