1036627-85-6

Basic information

• Product Name: N‐(2‐chlorobenzyl)benzo[d]thiazol‐2‐amine
• Synonyms: N‐(2‐chlorobenzyl)benzo[d]thiazol‐2‐amine
• CAS NO: 1036627-85-6
• Molecular Weight: 274.774
• Mol File: 1036627-85-6.mol

Chemical Properties

• CAS DataBase Reference: N‐(2‐chlorobenzyl)benzo[d]thiazol‐2‐amine(CAS DataBase Reference)
• NIST Chemistry Reference: N‐(2‐chlorobenzyl)benzo[d]thiazol‐2‐amine(1036627-85-6)
• EPA Substance Registry System: N‐(2‐chlorobenzyl)benzo[d]thiazol‐2‐amine(1036627-85-6)

Safety Data

• Hazardous Substances Data: 1036627-85-6(Hazardous Substances Data)

Upstream product

• 136-95-8 2-amino-benzthiazole 
• 17849-38-6 2-Chlorobenzyl alcohol 
• 103-72-0 phenyl isothiocyanate 
• 89-97-4 2-CHLOROBENZYLAMINE 
• 107135-19-3 N’-(2-chlorobenzylidene)-4-methylbenzenesulfonohydrazide 

Relevant articles and documents

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.

Metal-Free Synthesis of 2-Aminobenzothiazoles via Iodine-Catalyzed and Oxygen-Promoted Cascade Reactions of Isothiocyanatobenzenes with Amines

In this paper, a highly efficient and sustainable synthesis of 2-aminobenzothiazoles through the cascade reactions of isothiocyanatobenzenes with primary or secondary amines by using iodine as a catalyst and oxygen as an oxidant is presented. Mechanistically, the formation of the title compounds involves the in situ formation of the required benzothiourea intermediate followed by its intramolecular cross dehydrogenative coupling of a C(sp2)-H bond and a S-H bond. To our knowledge, this should be the first example in which 2-aminobenzothiazoles are efficiently prepared from simple and cheap isothiocyanates and amines under metal-free conditions by using iodine as a catalyst and molecular oxygen as an oxidant with water as the byproduct. Compared with literature protocols, this method eliminates the use of ortho-halo-substituted precursors, expensive transition-metal catalysts, and hazardous oxidants.

Synthesis method of 2-aminobenzothiazole compounds

The invention discloses a preparation method of 2-aminobenzothiazole compounds. The 2-aminobenzothiazole compounds is prepared from the following steps of dissolving phenyl/naphthalene isothiocyanateand primary amine into a solvent, adding a catalyst iodine and an oxidant, carrying out one-pot multi-step tandem reaction to prepare the 2-aminobenzothiazole compounds under the temperature of 80 to 150 DEG C. The synthesis method has the advantages that raw materials are cheap and easily available, the reaction condition is mild, the substrate application range is broad, atom economy is high, requirements of green chemical are met, and a novel method which is economical and practical and green and environmentally friendly is provided for synthesis of the 2-aminobenzothiazole compounds.

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.

Structure-dependent tautomerization induced catalyst-free autocatalyzed N-alkylation of heteroaryl amines with alcohols

Catalyst-free autocatalyzed dehydrative N-alkylation reactions of 2-aminobenzothiazoles, 2-aminopyrimidines, and 2-aminopyrazine with primary and secondary alcohols have been achieved for efficient, practical, and green synthesis of the versatile heteroaryl amine derivatives. These reactions were interestingly induced by structure-dependent tautomeric equilibria of the heteroaryl amines via MPV-O transfer hydrogenation of the imino tautomers by alcohols to give aldehydes as the key initiating step.

Sodium hydroxide catalyzed N-alkylation of (hetero) aromatic primary amines and N1,C5-dialkylation of 4-phenyl-2-aminothiazoles with benzyl alcohols

In the presence of a catalytic amount of NaOH, the selective N-alkylation of various heteroaromatic primary amines is reported. With 1 equiv of NaOH, N1,C5-dialkylation of 4-phenyl-2-aminothiazoles has been investigated. Reaction of in situ generated aldehyde with amine yields the N-alkylated and N1,C5-dialkylated products through hydride ion transformation from alcohol.

Direct N-alkylation of amino-azoles with alcohols catalyzed by an iridium complex/base system

The direct and regioselective N-alkylation of amino-azoles to the corresponding 2-N-(alkylamino)azoles using various alcohols as alkylating agents with good to excellent yields has been accomplished by an iridium complex/base system.

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.