N,N-Dibenzyl-2-chloroacetamide

Base Information

• Chemical Name: N,N-Dibenzyl-2-chloroacetamide
• CAS No.: 2567-51-3
• Molecular Formula: C16H16ClNO
• Molecular Weight: 273.762
• NSC Number: 2374
• DSSTox Substance ID: DTXSID90277446
• Nikkaji Number: J3.336.365F
• Wikidata: Q82008610
• Mol file: 2567-51-3.mol

Synonyms:N,N-DIBENZYL-2-CHLOROACETAMIDE;2567-51-3;ACETAMIDE,2-CHLORO-N,N-BIS(PHENYLMETHYL)-;N,N-DIBENZYL-2-CHLORO-ACETAMIDE;NSC2374;N,N-Dibenzylchloroacetamide;chloro-acetic acid dibenzylamide;SCHEMBL5451636;DTXSID90277446;ADAL1038594;NSC 2374;NSC-2374;MFCD00032566;STL284198;AKOS001042951;Acetamide, 2-chloro-N,N-bis(phenylmethyl)-

Chemical Property of N,N-Dibenzyl-2-chloroacetamide

Chemical Property:

• Vapor Pressure: 1.14E-07mmHg at 25°C
• Refractive Index: 1.589
• Boiling Point: 432.1 °C at 760 mmHg
• Flash Point: 215.1 °C
• PSA: 20.31000
• Density: 1.181 g/cm³
• LogP: 3.45420
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 5
• Exact Mass: 273.0920418
• Heavy Atom Count: 19
• Complexity: 250

Purity/Quality:

99% ^*data from raw suppliers

N,N-DIBENZYL-2-CHLORO-ACETAMIDE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CN(CC2=CC=CC=C2)C(=O)CCl
• Uses: N,N-Dibenzyl-2-chloroacetamide (cas# 2567-51-3) is a useful reactant for the diastereo-/chemoselective preparation of vinyl silanes/silyl-substituted alpha, beta-unsaturated amides by Pd-catalyzed olefination.

Technology Process of N,N-Dibenzyl-2-chloroacetamide

There total 4 articles about N,N-Dibenzyl-2-chloroacetamide 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%

chloroacetyl chloride (79-04-9) + dibenzylamine (103-49-1) → 2-chloro-N,N-bis(phenylmethyl)acetamide (2567-51-3)

Guidance literature:

With triethylamine; In diethyl ether; at 20 ℃; for 8h;

DOI:10.1021/jo8002166

Reference yield:

2-bromoacetyl chloride (22118-09-8) + dibenzylamine (103-49-1) → 2-chloro-N,N-bis(phenylmethyl)acetamide (2567-51-3)

Guidance literature:

In dichloromethane; at 0 - 20 ℃; for 3.5h; Inert atmosphere;

DOI:10.1002/anie.201405508

Reference yield:

monochloroacetic acid anhydride (4015-58-1) + dibenzylamine (103-49-1) → 2-chloro-N,N-bis(phenylmethyl)acetamide (2567-51-3)

Guidance literature:

upstream raw materials:

chloroacetyl chloride

dibenzylamine

monochloroacetic acid anhydride

2-bromoacetyl chloride

Downstream raw materials:

N,N-Dibenzyl-5-amino-3-thiapentanoic Acid Amide

N,N-dibenzylacetamide

N,N-dibenzyl-α-(methoxycarbonyl)acetamide

1,4-dihydro-2-(phenylmethyl)-3(2H)-isoquinolinone

Refernces

• 1、 Mu, Qiu-Chao,Wang, Xing-Ben,Ye, Fei,Sun, Yu-Li,Bai, Xing-Feng,Chen, Jing,Xia, Chun-Gu,Xu, Li-Wen. "Palladium-catalyzed olefination of aryl/alkyl halides with trimethylsilyldiazomethane via carbene migratory insertion". supporting information. p. 12994 - 12997. Retrieved 2018/11/23.
• 2、 Pedroni, Julia,Boghi, Michele,Saget, Tanguy,Cramer, Nicolai. "Access to β-lactams by enantioselective palladium(0)-catalyzed C(sp3)-H alkylation". supporting information. p. 9064 - 9067. Retrieved 2014/09/17.