5-Acetamido-1,3,4-thiadiazole-2-sulfonyl chloride

Base Information

• Chemical Name: 5-Acetamido-1,3,4-thiadiazole-2-sulfonyl chloride
• CAS No.: 32873-57-7
• Molecular Formula: C4H4 Cl N3 O3 S2
• Molecular Weight: 241.679
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID60186536
• Wikidata: Q83057852
• Mol file: 32873-57-7.mol

Synonyms:2-acetamine-5-sulfochloride-1,3,4-thiadiazole;sulfohydrazide

Chemical Property of 5-Acetamido-1,3,4-thiadiazole-2-sulfonyl chloride

Chemical Property:

• Melting Point: 230 °C
• PKA: 8.58±0.50(Predicted)
• PSA: 129.13000
• Density: 1.788±0.06 g/cm3(Predicted)
• LogP: 2.15430
• Solubility.: Methanol; DMSO; DMF
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 240.9382610
• Heavy Atom Count: 13
• Complexity: 300

Purity/Quality:

99%, ^*data from raw suppliers

5-(Acetylamino)-1,3,4-thiadiazole-2-sulfonylChloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC1=NN=C(S1)S(=O)(=O)Cl
• Uses: 5-(Acetylamino)-1,3,4-thiadiazole-2-sulfonyl Chloride is an intermediate used in the synthesis of Bis[5-(acetylamino)-1,3,4-thiadiazole-2-sulfonyl]amine (B400160), which is an impurity of Acetazolamide (A161500). Acetazolamide EP Impurity F

Technology Process of 5-Acetamido-1,3,4-thiadiazole-2-sulfonyl chloride

There total 7 articles about 5-Acetamido-1,3,4-thiadiazole-2-sulfonyl chloride 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: 95.0%

N-[5-methylsulfanyl-1,3,4-thiadiazol-2-yl]-acetamide (38583-51-6) → 5-acetamido-1,3,4-thiadiazolyl-2-sulfonyl chloride (32873-57-7)

Guidance literature:

N-[5-methylsulfanyl-1,3,4-thiadiazol-2-yl]-acetamide; With potassium nitrate; at 6 ℃; for 2.33333h;

With 3-monochlorophenol; lanthanum(III) nitrate; at 4 ℃; for 4.33333h; Temperature;

Reference yield: 80.0%

2-acetylamino-5-mercapto-1,3,4-thiadiazole (32873-56-6) → 5-acetamido-1,3,4-thiadiazolyl-2-sulfonyl chloride (32873-57-7)

Guidance literature:

With chlorine; acetic acid; at 0 - 2 ℃; for 2h;

DOI:10.1016/j.ejmech.2006.03.027

Reference yield:

acetic acid (64-19-7,77671-22-8) + 2-Amino-5-mercapto-1,3,4-thiadiazole (2349-67-9) → 5-acetamido-1,3,4-thiadiazolyl-2-sulfonyl chloride (32873-57-7)

Guidance literature:

With chlorine; In water; Cooling with ice;

upstream raw materials:

NSC 327174

2-acetamido-5-mercapto-1,3,4-thiazole

2-acetylamino-5-mercapto-1,3,4-thiadiazole

acetic acid

Downstream raw materials:

acetazolamide

Refernces

• 1、 -. "Preparation process for intermediate of acetazolamide". Paragraph 0051. . Retrieved 2017/09/13.
• 2、 Loghmani-Khouzani, Hossein,Rauckyte, Teresa,Osmialowski, Borys,Gawinecki, Ryszard,Kolehmainen, Erkki. "GIAO/DFT 13C NMR Chemical Shifts of 1,3,4-thiadiazoles". . p. 2217 - 2225. Retrieved 2008/02/10.