39222-73-6

Usage

Uses

Used in Chemical Synthesis:
2-Amino-5-tert-butyl-1,3,4-thiadiazole is used as an intermediate in the production of Buthidazole, a compound with potential applications in various industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-Amino-5-tert-butyl-1,3,4-thiadiazole is used as a key component in the preparation of several compounds, including:
1. 9H-2,6-di-tert-butyl-9-(2-hydroxyphenyl)-bis(1,3,4-thia-diazolo)[3,2-a:3",2"-d]-1,3,5-triazin-8-ium chloride, which may have applications in the development of new pharmaceuticals.
2. 1,1-dimethyl-3-(5-tert-butyl-1,3,4-thiadiazol-2-yl)urea, a compound that could be utilized in the synthesis of pharmaceuticals with various therapeutic properties.
3. N-(5-tert-butyl-1,3,4-thiadiazol-2-yl)-2,4-dihydroxythiobenzamide, which may be involved in the creation of drugs targeting specific medical conditions.
Used in Corrosion Inhibition:
2-Amino-5-tert-butyl-1,3,4-thiadiazole is used as a corrosion inhibitor for brass in sea water samples, providing protection against the damaging effects of corrosion and extending the lifespan of brass components in marine environments.

InChI:InChI=1/C6H11N3S/c1-6(2,3)4-8-9-5(7)10-4/h1-3H3,(H2,7,9)

Upstream product

• 3282-30-2 pivaloyl chloride 
• 79-19-6 thiosemicarbazide 
• 75-98-9 Trimethylacetic acid 
• 630-19-3 pivalaldehyde 
• 42826-42-6 pivalohydrazide 
• 5362-74-3 pivalaldehyde N-tosylhydrazone 
• 333-20-0 potassium thioacyanate 

Downstream Products

• 535-65-9 4-amino-N-(5-tert-butyl-1,3,4-thiadiazol-2-yl)benzenesulfonamide 
• 95939-82-5 3-(5-tert-butyl-[1,3,4]thiadiazol-2-ylamino)-1,2-diphenyl-propan-1-one 
• 91960-11-1 4-(5-tert-butyl-[1,3,4]thiadiazol-2-ylsulfamoyl)-benzoic acid 
• 92440-11-4 N-(5-tert-butyl-[1,3,4]thiadiazol-2-yl)-4-methyl-benzamide 
• 93353-23-2 N-(5-tert-butyl-[1,3,4]thiadiazol-2-yl)-4-nitro-benzamide 
• 95502-05-9 N-(5-tert-Butyl-[1,3,4]thiadiazol-2-yl)-4-nitro-benzamidine 
• 93258-11-8 4-amino-N-(5-tert-butyl-[1,3,4]thiadiazol-2-yl)-benzamide 
• 432509-85-8 N-(5-tert-butyl-1,3,4-thiadiazol-2-yl)-5-chloro-2-methoxybenzamide 
• 1190128-76-7 Br^(1-)*C₂₀H₂₆N₅S₂⁽¹⁺⁾ 
• 1190128-87-0 Br^(1-)*C₁₉H₂₄N₅OS₂⁽¹⁺⁾ 
• 1191951-67-3 N-(4-(N-(5-tert-butyl-1,3,4-thiadiazol-2-yl)sulfamoyl)phenyl)decanamide 

Relevant academic research and scientific papers

Diversity-Oriented Synthesis of 1,2,4-Triazols, 1,3,4-Thiadiazols, and 1,3,4-Selenadiazoles from N-Tosylhydrazones

The diversity-oriented synthesis of 1,2,4-triazols, 1,3,4-thiadiazols, and 1,3,4-selenadiazoles from N-tosylhydrazones was developed, and the reactions were general for a wide range of substrates, in which NH2CN, KOCN, KSCN, and KSeCN were used as odorless sources. Two different pathways were proposed, and N-tosylhydrazonoyl chlorides were formed in situ in the presence of NCS.

Pd2(dba)3-catalyzed amination of C5-bromo-imidazo[2,1-b][1,3,4] thiadiazole with substituted anilines at conventional heating in Schlenk tube

An efficient Pd2(dba)3-catalyzed amination of C5-bromo-imidazo[2,1-b][1,3,4]thiadiazole using conventional heating is reported. The C5-bromoimidazo[2,1-b][1,3,4]thiadiazole was synthesized using a multistep approach which started by cyclization of thiosemicarbazide with a carboxylic acid to give 2-amino[1,3,4]thiadiazoles which were further treated with 2-haloketones to give imidazo[2,1-b][1,3,4]thiadiazoles. Then, the bromination of imidazothiadiazole was done using N-bromosuccinimide to give the C5-bromo-imidazo[2,1-b][1,3,4]thiadiazole. Afterward, various C-N bond-forming approaches were attempted such as SNAr, Cu(I), Cu(II), Pd(OAc)2, Pd2(dba)3 catalyst with different ligand, additive, base, solvent and temperature conditions. Out of various approaches used, only Buchwald Hartwig amination, performed with conventional heating, gave N-arylamine-5-imidazothiadiazoles. Then, 10 different anilines with different electron-withdrawing and donating groups at different positions were employed to examine the scope and limitations of the method. Salient features of this method include conventional heating in a Schlenk tube as the reaction condition, the absence of the use of toxic isocyanides, the wide nature of substituent tolerance with anilines, and moderately good product yields.

Method for synthesizing 2-methylamino-5-tert-butyl-1,3,4-thiadiazole

The invention provides a method for synthesizing 2-methylamino-5-tert-butyl-1,3,4-thiadiazole. The method comprises the steps that pivalic acid and hydrazine hydrate are taken as raw materials and subjected to a dehydration reaction to obtain an intermediate I; the intermediate I and a vulcanizing agent are subjected to a vulcanization reaction to obtain an intermediate II; the intermediate II issubjected to dehydration and ring closing to obtain an intermediate III; the intermediate III and paraformaldehyde are subjected to a condensation reaction to obtain an intermediate IV; and the intermediate IV is subjected to a reduction reaction to obtain the 2-methylamino-5-tert-butyl-1,3,4-thiadiazole. The problems in the prior art that reaction raw materials are not easy to obtain, the industrial operation is difficult, the reaction process is prone to causing environmental pollution and the like are solved, and the synthetic method which is easy in raw material obtaining, environmentallyfriendly in process and easy to industrialize is provided.

1. 2, 3 - thiadiazole - 5 - a amidine compound synthesis method

The invention discloses a novel method for synthesizing a 1,2,3-thiadiazole-5-formamidine compound. The target compound shown in general formula TDCA is prepared from a compound as shown in general formula M by virtue of a methylation reaction. The target component as shown in the general formula M is prepared from a compound as shown in general formula A and a compound as shown in general formula N by virtue of a condensation reaction, wherein during the methylation reaction, preferably, a catalyst is an organic metallic catalyst consisting of cuprous iodide and a ligand, namely 2,2,6,6-tetramethyl-3,5-heptadione; during the reaction, preferably, dimethylbenzene is taken as a solvent, and the optimum reaction temperature is 100-140 DEG C. The method disclosed by the invention is high in yield and more environment-friendly (as shown in Specification).

Synthesis of 2-amino-1,3,4-oxadiazoles and 2-Amino-1,3,4-thiadiazoles via sequential condensation and I2-mediated oxidative C-O/C-S bond formation

2-Amino-substituted 1,3,4-oxadiazoles and 1,3,4-thiadiazoles were synthesized via condensation of semicarbazide/thiosemicarbazide and the corresponding aldehydes followed by I2-mediated oxidative C-O/C-S bond formation. This transition-metal-free sequential synthesis process is compatible with aromatic, aliphatic, and cinnamic aldehydes, providing facile access to a variety of diazole derivatives bearing a 2-amino substituent in an efficient and scalable fashion.

Discovery of novel aminothiadiazole amides as selective EP3 receptor antagonists

This Letter discloses a series of 2-aminothiadiazole amides as selective EP3 receptor antagonists. SAR optimization resulted in compounds with excellent functional activity in vitro. In addition, efforts to optimize DMPK properties in the rat are discussed. These efforts have resulted in the identification of potent, selective EP3 receptor antagonists with excellent DMPK properties suitable for in vivo studies.

SUBSTITUTED QUINAZOLINE DERIVATIVES AND THEIR USE AS INHIBITORS

The use of a compound of formula (I) 1 or a salt, ester or amide thereof; where X is O, or S, S(O) or S(O)2, or NR6 where R6 is hydrogen or C1-6 alkyl,; R5 is an optionally substituted 5-membered heteroaromatic ring, R1, R2 ,R3, R4 are independently selected from various specified moieties, in the preparation of a medicament for use in the inhibition of aurora 2 kinase. Certain compounds are novel and these, together with pharmaceutical compositions containing them are also described and claimed

2-Acylaminothiazol-4-ylacetamides as post-emergent selective herbicides

A class of amides disclosed to be useful as selective post-emergent herbicides are those having the general structural formula STR1 in which R1 is hydrogen or lower alkyl, R2 is amino, lower alkyl, lower chloroalkyl, lower alkylamino, lower alkenylamino, lower alkoxy or C3 to C5 cycloalkyl and R3 is phenyl, thiazolyl, thiadiazolyl or lower alkyl-substituted, halogen-substituted or trifluoromethyl-substituted phenyl, thiazolyl or thiadiazolyl.