Tetramisole

Base Information

• Chemical Name: Tetramisole
• CAS No.: 5036-02-2
• Deprecated CAS: 6649-23-6,803614-33-7
• Molecular Formula: C11H12N2S
• Molecular Weight: 204.296
• Hs Code.: 2934100090
• European Community (EC) Number: 225-729-3
• NSC Number: 614927
• UNII: C8M7RFE4NO
• DSSTox Substance ID: DTXSID20860143
• Nikkaji Number: J25.630G
• Wikidata: Q27146858
• NCI Thesaurus Code: C95050
• ChEMBL ID: CHEMBL277775
• Mol file: 5036-02-2.mol

Synonyms:Nilverm;Tetramisole

Chemical Property of Tetramisole

Chemical Property:

• Appearance/Colour: white to off-white crystalline powder
• Melting Point: 87-89°
• Boiling Point: 344.4 °C at 760 mmHg
• PKA: 10.00±0.40(Predicted)
• Flash Point: 162.1 °C
• PSA: 40.90000
• Density: 1.32 g/cm³
• LogP: 2.32160
• Storage Temp.: 2-8°C
• Solubility.: DMSO; Methanol
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 204.07211956
• Heavy Atom Count: 14
• Complexity: 246

Purity/Quality:

99% ^*data from raw suppliers

6-Phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1CSC2=NC(CN21)C3=CC=CC=C3
• Uses: Tetramisol is an isolated intermediate in the synthesis of 4-Hydroxy-tetramisole (H595270), a metabolite of Tetramisole, an anthelmintic.

Technology Process of Tetramisole

There total 11 articles about Tetramisole 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%

tetramisole hydrochloride (5086-74-8,74191-78-9) → Tetramisole (5036-02-2)

Guidance literature:

With sodium hydroxide; In diethyl ether; water; at 20 ℃; for 0.5h; Inert atmosphere;

DOI:10.1021/jacs.9b04508

Reference yield: 91.58%

N-(2-chloroethyl)-α-(chloromethyl)benzylamine hydrochloride + thiourea (17356-08-0) → Tetramisole (5036-02-2)

Guidance literature:

With sodium hydroxide; In aq. buffer; at 80 - 85 ℃; for 5.5h; pH=9; pH-value;

Reference yield: 87.54%

2-amino-4,5-dihydrothiazole hydrochloride (3882-98-2) + (1,2-dibromoethyl)benzene (102921-26-6,93-52-7) → Tetramisole (5036-02-2)

Guidance literature:

2-amino-4,5-dihydrothiazole hydrochloride; (1,2-dibromoethyl)benzene; With sodium carbonate; In N,N-dimethyl-formamide; at 85 ℃; for 2h;

In N,N-dimethyl-formamide; at 160 ℃; for 16h; Temperature; Reagent/catalyst;

upstream raw materials:

2-imino-3-(2-hydroxy-2-phenylethyl)thiazolidine

2-(2-imino-thiazolidin-3-yl)-1-phenyl-ethanone; hydrobromide

α-bromoacetophenone

2-[2-(2-hydroxy-2-phenyl-ethylamino)-ethyl]-isothiourea

Downstream raw materials:

1,3-bis-(4-chloro-phenyl)-6-phenyl-tetrahydro-thiazolo[2',3':2,3]imidazo[1,2-a][1,3,5]triazine-2,4-dione

6-phenyl-7-(toluene-4-sulfonylcarbamoyl)-2,3,5,6-tetrahydro-imidazo[2,1-b]thiazolium betaine

7-[(3,4-dichloro-phenyl)-thiocarbamoyl]-6-phenyl-2,3,5,6-tetrahydro-imidazo[2,1-b]thiazolium betaine

1,3-dimethyl-6-phenyl-tetrahydro-thiazolo[2',3':2,3]imidazo[1,2-a][1,3,5]triazine-2,4-dione

Refernces

Synthesis, antifungal and nematocidal activities of thioureines with an aminoester sequence

10.1016/0223-5234(96)88299-7

This research presents the synthesis, antifungal, and anthelmintic activities of twenty-three arylthioureines, which were designed with p-alanine or γ-aminobutyric alkyl ester chains. The purpose of the study was to evaluate the in vitro efficacy of these compounds against 44 strains of fungi and two genera of nematodes. The findings indicated that nitro derivatives were particularly potent against Aspergillus and Candida strains, while ester chains enhanced activity against the filarial worm Molinema dessetae. Twelve compounds showed an EC50 of less than 40 μg/ml, yet their anthelmintic potency was found to be weaker compared to tetramisole. The chemicals used in the synthesis process included aromatic amines, isothiocyanates, and aminoesters of p-alanine or GABA, with the final thioureine compounds being characterized by various substituents on the phenyl ring and different alkyl ester groups.

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