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Upstream product

• 136-95-8 2-amino-benzthiazole 
• 459-57-4 4-fluorobenzaldehyde 
• 459-56-3 4-fluorobenzylic alcohol 
• 210422-66-5 4-fluorobenzaldehyde p-toluenesulfonylhydrazone 
• 140-75-0 para-fluorobenzylamine 
• 1642135-31-6 C₁₄H₁₀FIN₂ 

Relevant academic research and scientific papers

Synthetic method for N-alkyl(benzo)thiazole

The invention provides a synthetic method for N-alkyl(benzo)thiazole. The synthetic method comprises the following steps: putting 0.4-0.8 mmol of a carbonyl compound, 0.4-0.8 mmol of p-toluenesulfonylhydrazide and 4-10 mL of a solvent in a flask and carrying out a reaction at 30 DEG C to 80 DEG C for 1 to 3 h; adding 0.4 mmol of 2-aminothiazole, 0.4-0.8 mmol of metal copper salt and 0.4-1.2 mmolof an alkali substance into the above reaction system, carrying out heating to 100 DEG C to 150 DEG C, and continuing the reaction for 2 h to 5 h; terminating the reaction to obtain a reaction productA; and subjecting the product A to purification and impurity separation so as to obtain pure N-alkyl(benzo)thiazole. According to the invention, the intermediate sulfonyl hydrazone is prepared from the carbonyl compound and sulfonyl hydrazide, and reacts with a 2-aminothiazole substance in the presence of a catalyst and under alkali conditions to obtain N-alkyl(benzo)thiazole. The synthetic method of the invention has the advantages of simple operation, low cost, high product yield and wide application range of a substrate. At the same time, the established method can also realize the synthesis of the anti-inflammatory drug fanetizole, and thus has high practical value.

Copper-catalyzed one-pot coupling reactions of aldehydes (ketones), tosylhydrazide and 2-amino(benzo)thiazoles: An efficient strategy for the synthesis of N-alkylated (benzo)thiazoles

An efficient and practical C–N bond formation methodology for the synthesis of N-alkylated (benzo)thiazoles was developed, via the copper-catalyzed one-pot two-step reactions of 2-amino(benzo)thiazoles and aldehydes (ketones) with tosylhydrazide. This cross-coupling reaction proceeded smoothly and tolerated a broad range of functional groups (46 examples). A variety of functionalized N-alkylated (benzo)thiazoles were obtained in moderate to high yields. Notably, gram-scale synthesis of fanetizole (anti-inflammatory drug) was also realized through this protocol.

Method for synthesizing substituent miscellaneous aromatic amine through reaction between miscellaneous aromatic amine and amine

The invention discloses a method for synthesizing substituent miscellaneous aromatic amine through a reaction between miscellaneous aromatic amine and amine. Inorganic base serves as an accelerant. The miscellaneous aromatic amine and the amine are directly subjected to the de-ammonia gas alkylation reaction, N-substituent miscellaneous aromatic amine ramifications are obtained, the reaction temperature ranges from 130 DEG C to 200 DEG C, the reaction time ranges from 24 hours to 48 hours, and the by-product is ammonia gas. According to the technical scheme, the inorganic base serves as the accelerant, the amine low in price and easy to get serves as an alkylation reagent, under the solvent-free conditions of nitrogen protection and sealing, the miscellaneous aromatic amine and the amine are subjected to the de-ammonia gas N-alkylation reaction, and the N-substituent miscellaneous aromatic amine ramifications can be obtained through direct synthesizing. The reaction method is direct, conditions are simple, operation is easy, the by-product is ammonia gas, less pollution is caused, and the ammonia gas can be recycled.

Copper-catalyzed synthesis of 2-aminobenzothiazoles from carbodiimide and sodium hydrosulfide

An efficient copper-catalyzed method for the synthesis of a variety of 2-aminobenzothiazoles has been developed. The reaction proceeded from carbodiimide and sodium hydrosulfide via a tandem reaction in the presence of copper(ii) trifluoromethanesulfonate to afford the corresponding 2-aminobenzothiazole derivatives in good to perfect yields. This journal is the Partner Organisations 2014.

Novel solid-phase parallel synthesis of N-substituted-2-aminobenzo [d]thiazole derivatives via cyclization reactions of 2-iodophenyl thiourea intermediate resin

A novel solid-phase methodology has been developed for the synthesis of N-alkyl, N-acyl, and N-sulfonyl-2-aminobenzo[d]thiazole derivatives. The key step in this procedure involves the preparation of polymer-bound 2-aminobenzo[d]thiazole resins 5 by cyclization reaction of 2-iodophenyl thiourea resin 3. The resin-bound 2-iodophenyl thiourea 3 is produced by addition of 2-iodophenyl isothiocyanate 2 to the amine-terminated linker amide resin 1. These core skeleton 2-aminobenzo[d]thiazole resins 5 undergo functionalization reactions with various electrophiles, such as alkyl halides, acid chlorides, and sulfonyl chlorides to generate N-alkyl, N-acyl, and N-sulfonyl-2-aminobenzo[d]thiazole resins 6, 7, and 8, respectively. Finally, N-alkyl, N-acyl, and N-sulfonyl-2-aminobenzo[d]thiazole derivatives 9, 10, and 11 are then generated in good yields and purities by cleavage of the respective resins 6, 7, and 8 using trifluoroacetic acid (TFA) in dichloromethane (DCM).

Regioselective N-alkylation of 2-aminobenzothiazoles with benzylic alcohols

The preparation of 2-(N-alkylamino)benzothiazoles via regioselecive N-alkylation of 2-aminobenzothiazoles has been accomplished by using benzylic alcohols as alkylating agents.