N-(6-nitro-1,3-benzothiazol-2-yl)acetamide

Base Information

• Chemical Name: N-(6-nitro-1,3-benzothiazol-2-yl)acetamide
• CAS No.: 80395-50-2
• Molecular Formula: C9H7N3O3S
• Molecular Weight: 237.23500
• Hs Code.: 2934200090
• European Community (EC) Number: 659-602-2
• DSSTox Substance ID: DTXSID30352660
• Nikkaji Number: J3.380.154H
• Wikidata: Q27455937
• ChEMBL ID: CHEMBL1213041
• Mol file: 80395-50-2.mol

Synonyms:N-(6-nitro-1,3-benzothiazol-2-yl)acetamide;80395-50-2;Acetamide, N-(6-nitro-2-benzothiazolyl)-;CHEMBL1213041;N-(6-Nitro-1,3-Benzothiazol-2-Yl)ethanamide;N-(6-Nitrobenzo[d]thiazol-2-yl)acetamide;N-{6-nitro-1,3-benzothiazol-2-yl}acetamide;n-(6-nitro-2-benzothiazolyl)acetamide;Oprea1_073822;SCHEMBL3924050;DTXSID30352660;BDBM50548162;STK175583;AKOS000644243;SS-5233;PMID28766366-Compound-Scheme15-3;CS-0313877;AE-641/30076025;EN300-11701030;SR-01000391692;SR-01000391692-1;Q27455937;Z26718826;5PW

Chemical Property of N-(6-nitro-1,3-benzothiazol-2-yl)acetamide

Chemical Property:

• PSA: 119.54000
• LogP: 3.33560
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 237.02081227
• Heavy Atom Count: 16
• Complexity: 307

Purity/Quality:

99% ^*data from raw suppliers

N-(6-Nitro-1,3-benzothiazol-2-yl)acetamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC1=NC2=C(S1)C=C(C=C2)[N+](=O)[O-]

Technology Process of N-(6-nitro-1,3-benzothiazol-2-yl)acetamide

There total 7 articles about N-(6-nitro-1,3-benzothiazol-2-yl)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: 96.0%

N-(4-nitrophenyl)-N'-acetylthiourea (66934-12-1) → N-(6-nitro-1,3-benzothiazol-2-yl)acetamide (80395-50-2)

Guidance literature:

With copper(l) iodide; caesium carbonate; L-proline; palladium dichloride; In dimethyl sulfoxide; at 100 ℃; for 8h;

DOI:10.1016/j.cclet.2015.08.001

Reference yield: 92.0%

2-amino-6-nitrobenzothiazole (6285-57-0) + acetic anhydride (108-24-7) → N-(6-nitro-1,3-benzothiazol-2-yl)acetamide (80395-50-2)

Guidance literature:

With pyridine; In acetone; for 8h; Reflux;

DOI:10.1002/cmdc.201700229

Reference yield: 90.0%

2-amino-6-nitrobenzothiazole (6285-57-0) + acetyl chloride (75-36-5) → N-(6-nitro-1,3-benzothiazol-2-yl)acetamide (80395-50-2)

Guidance literature:

With triethylamine; In 1,4-dioxane; at 0 - 20 ℃;

DOI:10.1021/acsmedchemlett.0c00416

upstream raw materials:

2-amino-6-nitrobenzothiazole

acetic anhydride

2-amino-benzthiazole

p-nitrophenylthiourea

Downstream raw materials:

6-nitro-[3-(furan-2-yl)-prop-2-eneamido]benzothiazole

6-nitro-[3-(3-hydroxy-4-methoxyphenyl)-prop-2-eneamido]-benzothiazole

6-nitro-[3-(4-chlorophenyl)-prop-2-eneamido]benzothiazole

6-nitro-[3-phenyl-prop-2-eneamido]benzothiazole

Refernces

• 1、 -. "NOVEL HYDRAZONE DERIVATIVE WITH ARYL OR HETEROARYL GROUP SUBSTITUTED AT TERMINAL AMINE GROUP THEREOF AND USE THEREOF". Paragraph 0261. . Retrieved 2021/11/04.
• 2、 Pugh, Kyler W.,Zhang, Zheng,Wang, Jian,Xu, Xiuzhi,Munthali, Vitumbiko,Zuo, Ang,Blagg, Brian S. J.. "From Bacteria to Cancer: A Benzothiazole-Based DNA Gyrase B Inhibitor Redesigned for Hsp90 C-Terminal Inhibition". supporting information. p. 1535 - 1538. Retrieved 2020/10/12.