5-Chlorothiophene-2-carboxamide

Base Information

• Chemical Name: 5-Chlorothiophene-2-carboxamide
• CAS No.: 22353-82-8
• Molecular Formula: C5H4ClNOS
• Molecular Weight: 161.612
• Hs Code.: 2934999090
• ChEMBL ID: CHEMBL3608990
• DSSTox Substance ID: DTXSID10409141
• Nikkaji Number: J2.774.303J
• Wikidata: Q27460402
• Mol file: 22353-82-8.mol

Synonyms:5-chlorothiophene-2-carboxamide;22353-82-8;5-chloro-2-thiophenecarboxamide;CHEMBL3608990;SCHEMBL92875;DTXSID10409141;OMOBWMBJNNCUFO-UHFFFAOYSA-N;2-Chloro-5-(carboxamido)thiophene;XAA35382;BDBM50115490;MFCD01922226;AKOS000278666;SB67029;CS-0157773;FT-0680149;D81731;1T-0800;J-517420;Q27460402;FQI

Chemical Property of 5-Chlorothiophene-2-carboxamide

Chemical Property:

• Vapor Pressure: 0.00447mmHg at 25°C
• Melting Point: 179-181°
• Refractive Index: 1.619
• Boiling Point: 277.623 °C at 760 mmHg
• PKA: 15.55±0.50(Predicted)
• Flash Point: 121.702 °C
• PSA: 71.33000
• Density: 1.475 g/cm³
• LogP: 2.20070
• Storage Temp.: 2-8°C
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 160.9702126
• Heavy Atom Count: 9
• Complexity: 130

Purity/Quality:

98%Min ^*data from raw suppliers

5-Chloro-2-thiophenecarboxamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(SC(=C1)Cl)C(=O)N
• Uses: 5-Chloro-2-thiophenecarboxamide is a metabolite of Rivaroxaban (R538000) which is a novel antithrombotic agent. Rivaroxaban is also a highly potent and selective, direct FXa inhibitor.

Technology Process of 5-Chlorothiophene-2-carboxamide

There total 9 articles about 5-Chlorothiophene-2-carboxamide 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: 94.0%

5-chlorothiophene-2-carbonyl chloride (42518-98-9) → 5-chlorothiophene-2-carboxamide (22353-82-8)

Guidance literature:

With ammonium hydroxide; In dichloromethane; at 20 ℃; Cooling with ice;

Reference yield: 80.0%

5-Chlorothiophene-2-carboxylic acid (24065-33-6) → 5-chlorothiophene-2-carboxamide (22353-82-8)

Guidance literature:

With ammonium hydroxide; In toluene; at 20 ℃; for 2h;

Reference yield: 80.0%

2-acetyl-5-chlorothiophene (6310-09-4) → 5-chlorothiophene-2-carboxamide (22353-82-8)

Guidance literature:

With ammonia; iodine; In water; at 60 ℃; for 1h;

DOI:10.1021/ol901250c

upstream raw materials:

2-thienyl chloride

carbamic chloride

(E)-N-[(5-chlorothiophen-2-yl)methylidene]hydroxylamine

5-Chloro-2-thiophenecarboxaldehyde

Downstream raw materials:

Rivaroxaban

5-chloro-N-((1-(4-(2-oxopyridin-1(2H)-yl)phenyl)-1H-imidazol-4-yl)methyl)thiophene-2-carboxamide methanesulfonate

5-chloro-N-((1-(4-(2-oxopyridin-1(2H)-yl)phenyl)-1H-imidazol-4-yl)methyl)thiophene-2-carboxamide thiocyanate

5-chloro-N-((1-(4-(2-oxopyridin-1(2H)-yl)phenyl)-1H-imidazol-4-yl)methyl)thiophene-2-carboxamide phosphate

Refernces

• 1、 Yu, Yongshi,Tazeem,Xu, Zhichao,Du, Liaoqi,Jin, Mengyu,Dong, Chune,Zhou, Hai-Bing,Wu, Shuwen. "Design and synthesis of heteroaromatic-based benzenesulfonamide derivatives as potent inhibitors of H5N1 influenza A virus". . p. 89 - 100. Retrieved 2019/01/30.
• 2、 -. "The preparation method of the [...] (by machine translation)". Paragraph 0049; 0050; 0051; 0052. . Retrieved 2018/11/22.