2-chloro-N-(4-sulfamoylphenyl)acetamide

Base Information

• Chemical Name: 2-chloro-N-(4-sulfamoylphenyl)acetamide
• CAS No.: 14949-01-0
• Molecular Formula: C8H9ClN2O3S
• Molecular Weight: 248.69
• Hs Code.: 2935009090
• European Community (EC) Number: 633-964-1
• NSC Number: 525660
• DSSTox Substance ID: DTXSID80326235
• Wikidata: Q82087042
• Mol file: 14949-01-0.mol

Synonyms:2-chloro-N-(4-sulfamoylphenyl)acetamide;14949-01-0;2-Chloro-N-(sulfamoylphenyl)acetamide;Acetamide,N-[4-(aminosulfonyl)phenyl]-2-chloro-;2-Chloro-N-(4-sulfamoyl-phenyl)-acetamide;N-[4-(Aminosulfonyl)phenyl]-2-chloroacetamide;NSC 525660;NSC525660;SCHEMBL7440868;DTXSID80326235;MFCD00034074;STK325976;AKOS000266814;NSC-525660;2-CHLORO-4'-SULFAMOYLACETANILIDE;LS-06272;UPCMLD0ENAT0501-4750:001;EN300-01924;SR-01000324379;SR-01000324379-1;Z56767798;F0307-0451

Chemical Property of 2-chloro-N-(4-sulfamoylphenyl)acetamide

Chemical Property:

• Melting Point: 217 °C
• Refractive Index: 1.617
• PKA: 9.87±0.12(Predicted)
• PSA: 97.64000
• Density: 1.527 g/cm³
• LogP: 2.36540
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 248.0022410
• Heavy Atom Count: 15
• Complexity: 317

Purity/Quality:

99% ^*data from raw suppliers

2-chloro-N-(4-sulfamoylphenyl)acetamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=CC=C1NC(=O)CCl)S(=O)(=O)N

Technology Process of 2-chloro-N-(4-sulfamoylphenyl)acetamide

There total 5 articles about 2-chloro-N-(4-sulfamoylphenyl)acetamide 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: 98.0%

sulfanilamide (63-74-1) + chloroacetyl chloride (79-04-9) → 2-chloro-N-(4-sulfamoylphenyl)acetamide (14949-01-0)

Guidance literature:

With potassium carbonate; In tetrahydrofuran; at 0 ℃;

DOI:10.1080/14756366.2017.1404593

Reference yield: 92.0%

sulfanilamide (63-74-1) → 2-chloro-N-(4-sulfamoylphenyl)acetamide (14949-01-0)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; chloroacetyl chloride; In dichloromethane; at 0 ℃; for 2.33h;

DOI:10.1039/d1md00187f

Reference yield: 80.0%

→ 2-chloro-N-(4-sulfamoylphenyl)acetamide (14949-01-0)

Guidance literature:

With 4-methyl-morpholine; In tetrahydrofuran; at 20 ℃; for 4h; Cooling with ice;

upstream raw materials:

sulfanilamide

chloroacetyl chloride

Chloroacetic anhydride

4-(2-aminoethyl)benzenesulfonamide

Downstream raw materials:

N-(N-propyl-glycyl)-sulfanilic acid amide

N-(3-methoxy-phenyl)-glycine-(4-sulfamoyl-anilide)

N-(N,N-diethyl-glycyl)-sulfanilic acid amide

2-(butylamino)-N-(4-sulfamoylphenyl)acetamide

Refernces

• 1、 Mishra, Chandra Bhushan,Kumari, Shikha,Angeli, Andrea,Monti, Simona Maria,Buonanno, Martina,Tiwari, Manisha,Supuran, Claudiu T.. "Discovery of Benzenesulfonamides with Potent Human Carbonic Anhydrase Inhibitory and Effective Anticonvulsant Action: Design, Synthesis, and Pharmacological Assessment". . p. 2456 - 2469. Retrieved 2017.
• 2、 Sa?l?k, Begüm Nurpelin,?evik, Ulviye Acar,Osmaniye,Levent, Serkan,?avu?o?lu, Betul Kaya,Demir,Ilg?n,?zkay,Koparal, Ali Sava?,Beydemir, ?ükrü,Kaplanc?kl?, Zafer As?m. "Synthesis, molecular docking analysis and carbonic anhydrase I-II inhibitory evaluation of new sulfonamide derivatives". . . Retrieved 2019.
• 3、 Arslan, Mustafa,Demir, Yeliz,Nixha, Arleta R.,Beydemir, ?ükrü,Istrefi, Q?ndresa,Küfrevio?lu, ?mer ?.,Türke?, Cüneyt. "Sulfonamides incorporating ketene N,S-acetal bioisosteres as potent carbonic anhydrase and acetylcholinesterase inhibitors". . . Retrieved 2020.
• 4、 Mboge, Mam Y.,Combs, Jacob,Singh, Srishti,Andring, Jacob,Wolff, Alyssa,Tu, Chingkuang,Zhang, Zaihui,McKenna, Robert,Frost, Susan C.. "Inhibition of Carbonic Anhydrase Using SLC-149: Support for a Noncatalytic Function of CAIX in Breast Cancer". . p. 1713 - 1724. Retrieved 2021.
• 5、 AboulMagd, Asmaa M.,Elsaadi, Mohamed T.,Hamed, Ahmed A.,Hamed, Mohamed I. A.,Hassan, Hossam M.,Nemr, Mohamed T. M.. "Design, synthesis and mechanistic study of new benzenesulfonamide derivatives as anticancer and antimicrobial agentsviacarbonic anhydrase IX inhibition". . p. 26241 - 26257. Retrieved 2021/08/13.