32873-57-7

Basic information

• Product Name: 2-(ACETAMIDO)-5-(CHLOROSULFONYL)-1,3,4-THIADIAZOLE
• Synonyms: 2-(ACETAMIDO)-5-(CHLOROSULFONYL)-1,3,4-THIADIAZOLE;2-(Acetamido)-5-(chlorosulfonyl)-1,3,4-thiadiazole 5-(Acetylamino)-1,3,4-thiadiazole-2-sulfonyl chloride;5-(acetylamino)-1,3,4-Thiadiazole-2-sulfonyl chloride;5-acetamido-1,3,4-thiadiazole-2-sulfonyl chloride
• CAS NO: 32873-57-7
• Molecular Formula: C₄H₄ClN₃O₃S₂
• Molecular Weight: 241.67586
• Mol File: 32873-57-7.mol

Chemical Properties

• Melting Point: 230 °C
• Appearance: /
• Density: 1.788±0.06 g/cm3(Predicted)
• Solubility: Methanol; DMSO; DMF
• PKA: 8.58±0.50(Predicted)
• CAS DataBase Reference: 2-(ACETAMIDO)-5-(CHLOROSULFONYL)-1,3,4-THIADIAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(ACETAMIDO)-5-(CHLOROSULFONYL)-1,3,4-THIADIAZOLE(32873-57-7)
• EPA Substance Registry System: 2-(ACETAMIDO)-5-(CHLOROSULFONYL)-1,3,4-THIADIAZOLE(32873-57-7)

Safety Data

• Hazardous Substances Data: 32873-57-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-(ACETAMIDO)-5-(CHLOROSULFONYL)-1,3,4-THIADIAZOLE is used as an intermediate in the synthesis of Bis[5-(acetylamino)-1,3,4-thiadiazole-2-sulfonyl]amine (B400160), which is an impurity of Acetazolamide (A161500). Acetazolamide is a medication used to treat glaucoma, epilepsy, and altitude sickness, among other conditions. 2-(ACETAMIDO)-5-(CHLOROSULFONYL)-1,3,4-THIADIAZOLE plays a crucial role in the development and production of this medication, ensuring its quality and efficacy.
Additionally, 2-(ACETAMIDO)-5-(CHLOROSULFONYL)-1,3,4-THIADIAZOLE may have potential applications in other industries, such as chemical synthesis or material science, where its unique properties could be utilized for various purposes.

Upstream product

• 32873-56-6 2-acetamido-5-mercapto-1,3,4-thiazole 
• 32873-56-6 2-acetylamino-5-mercapto-1,3,4-thiadiazole 
• 38583-51-6 N-[5-methylsulfanyl-1,3,4-thiadiazol-2-yl]-acetamide 
• 99055-56-8 NSC 327174 
• 108-24-7 acetic anhydride 
• 2349-67-9 2-Amino-5-mercapto-1,3,4-thiadiazole 
• 64-19-7 acetic acid 

Downstream Products

• 59-66-5 acetazolamide 

Relevant articles and documents

Synthetic method for drug intermediate 1,3,4-thiadiazole-2-acetamido-5-sulfonyl chloride

The invention discloses a synthetic method for the drug intermediate 1,3,4-thiadiazole-2-acetamido-5-sulfonyl chloride. The synthetic method comprises the following steps: adding 2-acetamido-5-thiomethyl-1,3,4-thiadiazole into a reaction vessel, controlling a temperature, adding a potassium nitrate solution, controlling a stirring speed and carrying out a reaction; and adding lanthanum nitrate inbatches, controlling the temperature, adding a 3-chlorophenol solution in batches within a certain period of time, continuing the reaction, adjusting the pH of value the obtained solution, allowing asolid to be precipitated, washing the solid with a sodium sulfate solution a plurality of times, then washing the solid with a cyclobutane solution a plurality of times, then washing the solid with amethylamine solution a plurality of times, carrying out recrystallization in a t-butanol solution, and then carrying out dehydration with a dehydrating agent so as to obtain the finished 1,3,4-thiadiazole-2-acetamido-5-sulfonyl chloride.

Preparation process for intermediate of acetazolamide

The invention especially relates to a preparation process for an intermediate of acetazolamide, belonging to the field of medicine synthesis. The process comprises the following steps: with thiosemicarbazide and carbon disulfide as reactants and a mixture of pyridine and piperidine as a solvent, carrying out a reaction; and then successively carrying out purification and drying so as to obtain 2-amino-5-mercapto-1,3,4-thiadiazole, i.e., the intermediate of acetazolamide.

Key intermediate aqiang 2-acetyl-5-chlorosulfonyl -1, 3, 4-thiadiazole method for preparing the non-chlorine (by machine translation)

The invention discloses a preparation method of non-chlorine gas of acetazolamide key intermediate 2-acetamido-5-chlorosulfonyl-1, 3, 4-thiadiazole. The preparation method comprises the steps of firstly adding hydrochloric acid into a reactor and then dropwise adding hydrogen peroxide to perform reaction so as to obtain a reaction solution; adding 2-acetamido-5-sulfydryl-1, 3, 4-thiadiazole into the obtained reaction solution in batch to perform reaction and obtaining a reactant after reaction is completed; directly conducting suction filtration, washing and drying on the reactant and performing drying to obtain the intermediate 2-acetamido-5-chlorosulfonyl-1, 3, 4-thiadiazole. The preparation method is more moderate in operate and more environment-friendly, and the obtained intermediate 2-acetamido-5-chlorosulfonyl-1, 3, 4-thiadiazole is good in color and luster and high in purity.

GIAO/DFT 13C NMR Chemical Shifts of 1,3,4-thiadiazoles

1H, 13C and 15N NMR spectra of 2-acetylamino-1,3,4-thiadiazole and its 5-substituted derivatives have been measured and assigned based on reference data, as well as homo- and heteronuclear 2 D NMR experiments. In addition, the GIAO/DFT approach at the B3LYP level of theory using the 6-311G basis set was used to calculate the 13C NMR chemical shifts. Although this method gives reliable results for 2-arylhydrazones of 1,3-diphenylpropanetrione, 2-phenacylpyridines, (Z)-2-(2-hydroxy-2-phenylvinyl)pyridines, 4-fluoroanilines, (1Z,3Z)-1,4-di(pyridin-2-yl)buta-1,3-dienediols and their tautomeric forms, the calculated chemical shifts for the 1,3,4-thiadiazoles studied are less satisfactory. Presence of the sulfur atom(s) seems to be responsible for such behavior.

Synthesis, antibacterial and?antitubercular activities of?some?7-[4-(5-amino-[1,3,4]thiadiazole-2-sulfonyl)-piperazin -1-yl] fluoroquinolonic derivatives

In the present study, a series of 7-[4-(5-amino-1,3,4 thiadiazole-2-sulfonyl)]-1-piperazinyl fluoroquinolonic derivatives VIIa-d were synthesized in good yields and characterized by IR, 1H-NMR, 13C-NMR, FAB Mass spectral and elemental analyses. The compounds were evaluated for their preliminary in vitro antibacterial activity against some Gram-positive and Gram-negative bacteria and selected compounds VIIa, b were screened for antitubercular activity against Mycobacterium tuberculosis H37Rv strain by broth dilution assay method. The antibacterial data of the tested N-sulfonylfluoroquinolones VIIa-d indicated that all the synthesized compounds showed better activity against Gram-positive bacteria S.?aureus, E.?faecelis, Bacillus sp. (MIC = 1-5?μg?ml-1, respectively) compared to reference drugs. The MIC values of tested derivatives connotes that the sparfloxacin and gatifloxacin derivatives VIIc, d were most active against the tested Gram-positive bacterial strains (MIC = 1-5?μg?ml-1). All the tested compounds VIIa-d showed poor activity against the Gram-negative bacteria. The in vitro antitubercular activity reports of selected compounds VIIa, b against M.?tuberculosis strain H37Rv showed moderate activity at MIC of 10?μg?ml-1.

Synthesis of certain diarylsulfonylureas as antitumor agents

A new series of N-aryl-N′-heteroaryl or N,N′-diheteroaryl sulfonylurea or sulfonylthiourea was synthesized and screened for their antitumor activity at the National Cancer Institute (NCI). N-(3-Chlorophenyl)-N′-(6-methyl-uracil-2-sulfonyl)urea (28) with GI50, TGI, LC50 (MG-MID) values of 66.1, 83.2, 93.3 μM, respectively is the most active compound in this study. It showed a remarkable activity more than sulofenur against HL-60 (TB) and RPMI-8226 leukemia, HOP-92 Non small lung cancer, KM12 colon cancer, SF-295 CNS cancer, PC-3 prostate cancer, OVCAR-4 Ovarian cancer, CAKI-1 and UO-31 Renal cancer, and MDA-MB-435 Breast cancer with GI50 values of 0.3, 2.7, 6.9, 14.7, 8.2, 9.3, 2.0, 2.1, 3.4, 11.3 μM, respectively.

Synthesis and investigation of inhibition effects of new carbonic anhydrase inhibitors

Three new derivatives of 2-substituted 1,3,4-thiadiazole-5-sulfonamide have been synthesized. These compounds are 2-(3-chloropropionylamino)- 1,3,4-thiadiazole-5-sulfonamide (1); 2-(2,2-dichloroacetylamino)-1,3,4-thiadiazole-5-sulfonamide (2); and 2-(3-phenylpropionylamino)-1,3,4-thiadiazole-5-sulfonamide (3). Inhibition effects of these compounds on carbonic anhydrase I and II have been investigated. By comparing 150 and K(i) values of the compounds, it has been found that compound 1 is a more potent inhibitor than acetazolamide (b) on carbonic anhydrase II.

Aminosulfonylthiadiazolylureas

Disclosed are compounds of the formula STR1 wherein R1 is alkyl, R2 is selected from the group consisting of hydrogen and alkyl; or R1 and R2 together with the nitrogen atom form a cyclic ring structure having 4 or 5 carbon atoms; m is the integer 0 or 1; when m is 1, R4 and R5 are each independently selected from the group consisting of hydrogen and alkyl or up to 3 carbon atoms; when m is 0, R4 is hydrogen and R5 is the same as defined above; R3, R6, R7, R8, R9 are each independently selected from the group consisting of hydrogen and alkyl; n is an integer from 0 to 2; and Z1 and Z2 are each independently selected from the group consisting of oxygen and sulfur. These compounds are useful as herbicides.