107167-61-3

Upstream product

• 110-91-8 morpholine 
• 463-71-8 thiophosgene 
• 107167-55-5 N-(p-tolyl)-N',N-dicarbomethoxyguanidine 
• 622-59-3 1-isothiocyanato-4-methylbenzene 
• 7175-47-5 4-methylphenyl isocyanide 
• 3085-54-9 N-(4-methylphenyl)formamide 
• 2740-81-0 2-chlorophenylisothiocyanate 
• 106-49-0 p-toluidine 

Downstream Products

• 1237747-19-1 N-((E)-(p-tolylimino)(morpholino)methyl)-N-p-tolylmorpholine-4-carbothioamide 
• 77475-91-3 C₂₄H₃₀N₄O₂S 
• 1162043-83-5 4-(6-methylbenzo[d]thiazol-2-yl)morpholine 

Relevant academic research and scientific papers

An isocyanide based multi-component reaction under catalyst- and solvent-free conditions for the synthesis of unsymmetrical thioureas

A new and efficient method for the synthesis of thiourea derivatives by a sequential one-pot, three-component reaction between aromatic isocyanides, amines, and 1,2-di-tert-butyldisulfane (DTBS) was developed and 27 different examples were synthesized in good to excellent yields. DTBS was identified as an effective sulfur surrogate without the use of both catalysts and solvents. This protocol does not employ any transition metal catalyst or special experimental setup.

Eosin y catalyzed visible-light-promoted aerobic oxidative cyclization of 2-aminobenzothiazole

A mild and efficient one-pot visible light irradiated synthesis of 2-aminobenzothiazole 4(a-l) from arylisothiocyanate 1(a-l) and secondary amines 2 have been reported in presence of eosin Y as an organophotoredox catalyst at room temperature under aerobi

Cu(ii) catalysed chemoselective oxidative transformation of thiourea to thioamidoguanidine/2-aminobenzothiazole

2-Haloaryl-sec-alkyl unsymmetrical thioureas (Tu) (halo = -F, -Cl) with a catalytic amount of Cu(ii) salt get oxidised in situ to their disulfide intermediates followed by an imine-disulfide rearrangement to give thioamidoguanidino (Tag) moieties at room temperature. During this process Cu(ii) gets reduced to Cu(i) and forms a complex with the Tag moiety from which Tag moiety can be isolated upon treatment with ammonia. However, when the same reaction was performed at an elevated temperature with a catalytic quantity of Cu(ii) salt, Tu bearing o-halogens (-F, -Cl) gave 2-aminobenzothiazoles via a dehalogenative heteroarylation path and not by the Hugerschoff path involving an electrophilic substitution reaction. For thioureas containing reactive ortho halogens (such as -Br, -I) the reaction proceeds at room temperature giving 2-aminobenzothiazoles via a dehalogenative path requiring a catalytic quantity of Cu(ii). No transformation of thiourea (Tu) to Tag was observed with Cu(i) salts suggesting the requirement of an oxidising Cu(ii) salt for this oxidative transformation. Mild reaction conditions, environmentally benign reagents and solvent, high yields, tolerance of various functional groups are some of the essential features of this methodology.

A ligand free copper(II) catalyst is as effective as a ligand assisted Pd(II) catalyst towards intramolecular C-S bond formation via C-H functionalization

Copper(I) catalysts are usually ineffective on the other hand Pd(II) catalysts are quite effective in promoting intramolecular sp2 C-H functionalization (C-S bond formation). Herein, we have developed a ligand assisted Pd(II) catalyzed C-S bond formation via C-H activation from arylthioureas leading to the formation of 2-aminobenzothiazoles for substrates bearing electron donating (EDG) groups in the aryl ring. However without the assistance of ligand this Pd(II) catalyzed reaction is quite unproductive particularly for thioureas possessing strongly electron donating groups in the aryl rings. Interestingly, the ligand free Cu(II) catalyzed oxidative cyclization of arylthioureas are equally effective both for arylthioureas possessing electron donating as well as electron withdrawing groups in the aryl rings.

Arylthioureas with bromine or its equivalents gives no 'Hugerschoff' reaction product

The in situ generated aryl-alkyl unsymmetrical thiourea obtained by the reaction of an aryl isothiocyanate with an aliphatic secondary amine on treatment with bromine or its equivalent gave exclusively a product having a thioamido guanidino moiety and not the expected Hugerschoff product 2-aminobenzothiazole. A plausible reaction mechanism has been proposed for this unprecedented transformation and the scope has been extended to various substrates. The Royal Society of Chemistry 2010.

Heterocycle formation via palladium-catalyzed intramolecular oxidative C-H bond functionalization: An efficient strategy for the synthesis of 2-aminobenzothiazoles

N-Arylthioureas are converted to 2-aminobenzothiazoles via Intramolecular C-S bond formation/C-H functionalization utilizing an unusual cocatalytic Pd(PPh3)4MnO2 system under an oxygen atmosphere at 80 °C. This method elim

Oxidation of thiocarbamyls with lead tetraacetate

Oxidation of a series of arylthiocarbamyls 2 to the corresponding bis-formamidinomonosulphides 3 with lead tetraacetate has been carried out. In addition sulphur is obtained.

Reaction of 1,4,2-Dithiazolium Salts with Amino Compounds

Systematic studies on the behavior of 1,4,2-dithiazolium cations (1) toward various amino compounds (ammonia, aliphatic and aromatic amines, hydrazine, semicarbazide, thiosemicarbazide derivatives, etc.) were performed.The reaction pathway could be classified into three types depending on possibile three fission modes of the initially-formed adduct.The main products were 5-imino-1,4,2-dithiazole, thiourea, and 1,3,4-thiadiazole derivatives, through the three different pathways, respectively.In order to clarify the factors controlling the reaction courses, the reactions of 1 with p-substituted aniline derivatives were carried out under systematically varying conditions.The strength of bases and the polaritiy of solvents had clear influence on the reactivity.The reaction mechanism is also discussed.

Fragmentation of N-aryl- and N-Aralkyl-N',N"-dicarbomethoxyguanidines with Thiophosgene

N-Aryl- and N-aralkyl-N',N"-dicarbomethoxyguanidines (3) on treatment with thiophosgene undergo fragmentation to yield N,N'-dicarbomethoxyurea (5) and the isothiocyanates.