19394-61-7

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 37, p. 1360, 1972 DOI: 10.1021/jo00974a016

InChI:InChI=1/C13H9NS/c15-10-14-13-9-5-4-8-12(13)11-6-2-1-3-7-11/h1-9H

Upstream product

• 90-41-5 2-phenylaniline 
• 463-71-8 thiophosgene 
• 2926-29-6 Langlois reagent 
• 871877-03-1 N,N'-bis-biphenyl-2-yl-thiourea 

Downstream Products

• 914638-57-6 3-(3-biphenyl-2-yl-thioureido)-6-chloro-2-hydroxy-N,N-dimethyl-benzenesulfonamide 
• 182572-34-5 N-(2-phenyl)phenyl-N'-(3-(1-methylpiperidin-4-yl)-1H-indol-5-yl)thiourea 
• 19250-02-3 N-<1,1'-biphenyl>-2-ylthiourea 

Relevant academic research and scientific papers

Organophosphine-free copper-catalyzed isothiocyanation of amines with sodium bromodifluoroacetate and sulfur

A copper-catalyzed isothiocyanation of amines with sodium bromodifluoroacetate and sulfur in the absence of organophosphine has been established. This approach represents a simple and efficient one-pot synthesis of isothiocyanates, and features excellent functional group tolerance and the use of a cheap, safe and odorless sulfur source. Moreover, this process could directly provide isothiocyanate analogous bioactive molecules, thiocarbonyl-containing pesticides and facile construction of benzoxazole and benzimidazole frames.

Isothiocyanate synthesized by three components and preparation method of isothiocyanate

The invention discloses isothiocyanate and a preparation method thereof. The method comprises the steps that primary amine, sodium difluorobromoacetate and elemental sulfur are taken as reactants forreaction; the reaction is carried out under the action of a copper catalyst, wherein the copper catalyst is any one of cuprous chloride, copper bromide, cuprous iodide, copper chloride and copper trifluoromethanesulfonate; an alkali is also added, wherein the alkali is any one of sodium bicarbonate, potassium carbonate, cesium carbonate, potassium phosphate, DABCO and sodium tert-butoxide; the whole reaction is carried out in a solvent, wherein the solvent is acetonitrile or dimethyl sulfoxide, the reaction temperature is 80-120 DEG C, and the reaction time is 10-14 hours. The method can directly synthesize the target product, does not need to separate intermediate products and only needs stirring and heating reaction under normal pressure to obtain the target product, and the yield can beup to 87%; a waste solution is fewer during the reaction, and the method protects the environment and ensures the health of an operator; in addition, a series of isothiocyanate derivatives can be prepared, and the method has a stronger substrate universality.

Isothiocyanation of amines using the Langlois reagent

The Langlois reagent was found to be effective for the isothiocyanation of primary amines in the presence of copper iodide and diethyl phosphonate.

A metal-free synthesis of 2-aminobenzothiazoles through aminyl radical addition to aryl isothiocyanates

A convenient synthesis of 2-aminobenzothiazoles, starting from aryl isothiocyanates and formamides under metal-free conditions, is described. Various secondary and tertiary amine- and even α-amino acid-derived formamides can be used as amino sources in this process. Mechanistic studies suggest that the reaction is initiated by decarbonylative aminyl radical formation in the presence of n-Bu4NI and TBHP, followed by aminyl radical addition to isothiocyanates and cyclization via sulfur centred radical intermediates.

Diversity-orientated synthesis of 3,5-bis(arylamino)pyrazoles

The synthesis of differentially-substituted 3,5-bis(arylamino)pyrazoles has not yet been documented. During our investigation, we managed to develop a novel, entirely combinatorial synthesis of 3,5-bis(arylamino)pyrazoles relying on a simple one-pot two-step operation.

2-Arylimino-5,6-dihydro-4H-1,3-thiazines as a new class of cannabinoid receptor agonists. Part 1: Discovery of CB2 receptor selective compounds

2-Arylimino-5,6-dihydro-4H-1,3-thiazines have been identified as a novel class of cannabinoid agonists. A lead structure with moderate activity was discovered through a high throughput screening assay. Structure-activity relationships led to the discovery of potent agonists of CB2 receptor. The most potent compound 13 displays Ki values of >5000 and 9 nM to CB1 and CB2 receptors, respectively.

Biphenyl-substituted guanidine derivatives useful as hypoglycaemic agents

Compounds of formula I STR1 and their salts in which R1 is optionally substituted phenyl, R2 is alkyl, cycloalkyl or optionally substituted amino, or R2 and R3 together with the nitrogen and carbon atoms to which they are attached form an optionally substituted heterocyclic ring or R3 and R4 together with the nitrogen atom to which they are attached form an optionally substituted heterocyclic ring and R5 is H, halo, alkyl, alkoxy, trifluoromethyl or a group of formula S(O)m R8 in which m is 0, 1 or 2 and R8 is alkyl have utility in the treatment of diabetes particularly in the treatment of hyperglycaemia.