N-[2-(4-Amino-phenyl)-acetyl]-methanesulfonamide

Base Information

• Chemical Name: N-[2-(4-Amino-phenyl)-acetyl]-methanesulfonamide
• CAS No.: 402508-82-1
• Molecular Formula: C9H12 N2 O3 S
• Molecular Weight: 228.272
• DSSTox Substance ID: DTXSID60453492
• Wikidata: Q82274641
• Mol file: 402508-82-1.mol

Synonyms:402508-82-1;N-[2-(4-AMINO-PHENYL)-ACETYL]-METHANESULFONAMIDE;SCHEMBL21887555;DTXSID60453492;2-(4-Aminophenyl)-N-(methylsulfonyl)acetamide;2-(4-Aminophenyl)-N-(methanesulfonyl)acetamide

Chemical Property of N-[2-(4-Amino-phenyl)-acetyl]-methanesulfonamide

Chemical Property:

• PSA: 101.13000
• LogP: 2.38940
• XLogP3: 0
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 228.05686342
• Heavy Atom Count: 15
• Complexity: 313

Purity/Quality:

N-[2-(4-amino-phenyl)-acetyl]-methanesulfonamide 95 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CS(=O)(=O)NC(=O)CC1=CC=C(C=C1)N

Technology Process of N-[2-(4-Amino-phenyl)-acetyl]-methanesulfonamide

There total 2 articles about N-[2-(4-Amino-phenyl)-acetyl]-methanesulfonamide 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: 91.7%

N-[2-(4-nitrophenyl)acetyl]methanesulfonamide (402508-74-1) → N-[2-(4-aminophenyl)acetyl]methanesulfonamide (402508-82-1)

Guidance literature:

With hydrogenchloride; palladium 10% on activated carbon; hydrogen; In ethanol; water; at 20 ℃;

Reference yield:

4-nitrobenzeneacetic acid (104-03-0) → N-[2-(4-aminophenyl)acetyl]methanesulfonamide (402508-82-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: CDI / CH₂Cl₂ / 1 h

1.2: CH₂Cl₂ / 1 h

1.3: 67 percent / DBU / CH₂Cl₂ / 16 h

2.1: H₂ / 10percent Pd/C / methanol / 7 h / 20 °C / 760.05 Torr

With hydrogen; 1,1'-carbonyldiimidazole; 10percent Pd/C; In methanol; dichloromethane;

DOI:10.1021/jm0101500

Reference yield: 95.0%

N-[2-(4-aminophenyl)acetyl]methanesulfonamide (402508-82-1) + 1,1-dimethylethyl ((2R)-2-(3-chlorophenyl)-2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}ethyl)[(1R)-1-methyl-2-oxoethyl]carbamate (174891-03-3) → tert-butyl (2R)-2-{[tert-butyl(dimethyl)silyl]oxy}-2-(3-chlorophenyl)ethyl[(1R)-1-methyl-2-(4-{2-[(methylsulfonyl)amino]-2-oxoethyl}anilino)ethyl]carbamate (402508-99-0)

Guidance literature:

With sodium tris(acetoxy)borohydride; In dichloromethane; N,N-dimethyl-formamide; at 20 ℃; for 60h;

DOI:10.1021/jm0101500

upstream raw materials:

N-[2-(4-nitrophenyl)acetyl]methanesulfonamide

4-nitrobenzeneacetic acid

Downstream raw materials:

tert-butyl (2R)-2-{[tert-butyl(dimethyl)silyl]oxy}-2-(3-chlorophenyl)ethyl[(1R)-1-methyl-2-(4-{2-[(methylsulfonyl)amino]-2-oxoethyl}anilino)ethyl]carbamate

Refernces

• 1、 Uehling, David E.,Donaldson, Kelly H.,Deaton, David N.,Hyman, Clifton E.,Sugg, Elizabeth E.,Barrett, David G.,Hughes, Robert G.,Reitter, Barbara,Adkison, Kim K.,Lancaster, Mary E.,Lee, Frank,Hart, Robert,Paulik, Mark A.,Sherman, Bryan W.,True, Timothy,Cowan, Conrad. "Synthesis and evaluation of potent and selective β3 adrenergic receptor agonists containing acylsulfonamide, sulfonylsulfonamide, and sulfonylurea carboxylic acid isosteres". . p. 567 - 583. Retrieved 2007/10/03.