N-methoxybenzamide

Base Information

• Chemical Name: N-methoxybenzamide
• CAS No.: 2446-51-7
• Molecular Formula: C8H9NO2
• Molecular Weight: 151.165
• ChEMBL ID: CHEMBL2436417
• DSSTox Substance ID: DTXSID70493682
• Nikkaji Number: J543.997C
• Wikidata: Q82340551
• Mol file: 2446-51-7.mol

Synonyms:N-methoxybenzamide;2446-51-7;N-methoxy-benzamide;Benzamide, N-methoxy-;SCHEMBL810200;SCHEMBL8773447;CHEMBL2436417;DTXSID70493682;PBQZQTQFQFYBNJ-UHFFFAOYSA-N;CAA44651;MFCD19439675;AKOS009129070;SB75875;AS-19791;CS-0155863;W17974;A822135;A912053;W-206894

Chemical Property of N-methoxybenzamide

Chemical Property:

• Melting Point: 63.5-64.5 °C
• PSA: 41.82000
• Density: 1?+-.0.06 g/cm3(Predicted)
• LogP: 1.55260
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 151.063328530
• Heavy Atom Count: 11
• Complexity: 130

Purity/Quality:

97% ^*data from raw suppliers

N-Methoxybenzamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CONC(=O)C1=CC=CC=C1

Technology Process of N-methoxybenzamide

There total 36 articles about N-methoxybenzamide 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-methoxylamine hydrochloride (593-56-6) + benzoyl chloride (98-88-4) → N-methoxybenzamide (2446-51-7)

Guidance literature:

With pyridine; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1016/j.tet.2004.02.048

Reference yield: 99.0%

N-methoxylamine hydrochloride (593-56-6) + benzoic acid (65-85-0,8013-63-6) → N-methoxybenzamide (2446-51-7)

Guidance literature:

With 1,1'-carbonyldiimidazole; In tetrahydrofuran; at 20 ℃;

DOI:10.1039/c9cc07173c

Reference yield: 91.0%

sodium benzoate (532-32-1) + N-methoxylamine hydrochloride (593-56-6) → N-methoxybenzamide (2446-51-7)

Guidance literature:

With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In water; acetonitrile; at 20 ℃; for 0.5h; Reagent/catalyst; Solvent; Green chemistry;

DOI:10.1039/d1ob02064a

upstream raw materials:

Ethyl (E)-O-Methylbenzohydroximate

Benzohydroxamic acid

methyl iodide

methyl bromide

Downstream raw materials:

N-Benzoyl-N-(2-propinyl)-O-methyl-hydroxylamin

benzoic acid ethyl ester

benzamide

O-methyl N-chlorobenzohydroxamate

Refernces

Mild rhodium(III)-catalyzed cyclization of amides with α,β- unsaturated aldehydes and ketones to azepinones: Application to the synthesis of the homoprotoberberine framework

10.1002/anie.201301426

The key substrate used in this study, N-methoxybenzamide (1a), is an amide with a methoxy group attached to the nitrogen atom. It is key for the initial reaction with a,b-unsaturated aldehydes and ketones. Another amide substrate used in this study, N-methylbenzamide (1b), has a methyl group attached to the nitrogen atom, which affects the reactivity and selectivity of the C-H activation process. N-n-butylbenzamide (1c), an amide with a butyl group attached to the nitrogen atom, demonstrates the versatility of the method towards different alkyl groups. N-benzylbenzamide (1d), an amide with a benzyl group attached to the nitrogen atom, is used to demonstrate the tolerance of the reaction towards aromatic groups. Acrolein (2a), the simplest unsaturated aldehyde used in this study, acts as the electrophilic component in the cyclization process and reacts with the amide to generate the desired azacyclopentane product.

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