Benzamide, N-cyclopropyl-N-methyl-

Base Information

• Chemical Name: Benzamide, N-cyclopropyl-N-methyl-
• CAS No.: 155940-92-4
• Molecular Formula: C₁₁H₁₃NO
• Molecular Weight: 175.23
• Mol file: 155940-92-4.mol

Synonyms:Benzamide, N-cyclopropyl-N-methyl-

Chemical Property of Benzamide, N-cyclopropyl-N-methyl-

Chemical Property:

• PSA: 20.31000
• LogP: 1.92100

Purity/Quality:

BENZAMIDE, N-CYCLOPROPYL-N-METHYL- 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Benzamide, N-cyclopropyl-N-methyl-

There total 5 articles about Benzamide, N-cyclopropyl-N-methyl- 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: 48.0%

2-iodo-N-cyclopropyl-N-methylbenzamide (1248615-31-7) → 2-methyl-2,5-dihydro-1H-benzo[c]azepin-1-one (1432371-82-8) + 2-methyl-2,3-dihydro-1H-benzo[c]azepin-1-one (1432371-85-1) + N-cyclopropyl-N-methylbenzamide (155940-92-4)

Guidance literature:

With silver orthophosphate; palladium diacetate; potassium carbonate; tri tert-butylphosphoniumtetrafluoroborate; In toluene; at 125 ℃; for 16h; Glovebox;

DOI:10.1016/j.tet.2013.02.080

Reference yield: 37.0%

cyclopropylboronic acid pinacol ester (126689-01-8) + N-methylbenzamide (88070-48-8) → N-cyclopropyl-N-methylbenzamide (155940-92-4)

Guidance literature:

With pyridine; oxygen; copper diacetate; caesium carbonate; In toluene; at 110 ℃; for 24h; Sealed tube;

DOI:10.1039/c3cc42575d

Reference yield:

2-Iodobenzoic acid (88-67-5) → 2-methyl-2,3-dihydro-1H-benzo[c]azepin-1-one (1432371-85-1) + N-cyclopropyl-N-methylbenzamide (155940-92-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: oxalyl dichloride; N,N-dimethyl-formamide / tetrahydrofuran / 0.75 h / 20 °C / Inert atmosphere

2.1: tetrahydrofuran / 0.17 h / Inert atmosphere

2.2: 16 h / 20 °C / Inert atmosphere

3.1: sodium hydride / tetrahydrofuran / 0.25 h / 0 °C

3.2: 16 h / 0 - 20 °C

4.1: palladium diacetate; tri tert-butylphosphoniumtetrafluoroborate; potassium carbonate; silver orthophosphate / toluene / 16 h / 125 °C / Glovebox

With silver orthophosphate; oxalyl dichloride; palladium diacetate; sodium hydride; potassium carbonate; N,N-dimethyl-formamide; tri tert-butylphosphoniumtetrafluoroborate; In tetrahydrofuran; toluene;

DOI:10.1016/j.tet.2013.02.080

upstream raw materials:

2-iodo-N-cyclopropyl-N-methylbenzamide

2-Iodobenzoic acid

N-Cyclopropyl-2-iodo-benzamide

2-Iodobenzoyl chloride

Refernces

• 1、 Racine, Emilie,Monnier, Florian,Vors, Jean-Pierre,Taillefer, Marc. "Direct N-cyclopropylation of secondary acyclic amides promoted by copper". supporting information. p. 7412 - 7414. Retrieved 2013/09/23.