18792-49-9

Usage

Chemical structure

A pyrrolidine derivative containing a phenylthiocarbamoyl group attached to the nitrogen atom of the pyrrolidine ring.

Applications

a. Intermediate in the synthesis of various pharmaceuticals and agrochemicals.
b. Building block for the creation of new organic molecules with biological activity.
c. Potential use as an insecticide and fungicide.

Structural versatility

Allows for the compound to be used in a wide range of chemical reactions and synthesis processes.

Reactivity

The presence of the phenylthiocarbamoyl group contributes to the compound's reactivity, making it a valuable intermediate in various chemical reactions.

Importance in fields

Chemistry and agriculture, due to its potential applications in the development of new pharmaceuticals, agrochemicals, and as a pesticide.

Biological activity

Has shown potential as a building block for creating new organic molecules with biological activity, which can be further explored for various applications in the pharmaceutical and agrochemical industries.

InChI:InChI=1/C11H14N2S/c14-11(13-8-4-5-9-13)12-10-6-2-1-3-7-10/h1-3,6-7H,4-5,8-9H2,(H,12,14)

Upstream product

• 123-75-1 pyrrolidine 
• 103-72-0 phenyl isothiocyanate 
• 2403-57-8 1-(2-methylprop-1-en-1-yl)pyrrolidine 
• 1197040-29-1 phenyl isocyanate 
• 103-70-8 Formanilid 
• 92147-65-4 tert-butyl phenylcarbamodithioate 
• 62-53-3 aniline 
• 4314-19-6 bis(1H-benzo[d][1,2,3]triazol-1-yl)methanethione 

Downstream Products

• 134720-33-5 4-Fluoro-N-phenyl-N-(pyrrolidine-1-carbothioyl)-benzamide 
• 134720-32-4 3-Chloro-N-phenyl-N-(pyrrolidine-1-carbothioyl)-benzamide 
• 134720-35-7 3,4,5-Trimethoxy-N-phenyl-N-(pyrrolidine-1-carbothioyl)-benzamide 
• 134720-31-3 N-Phenyl-N-(pyrrolidine-1-carbothioyl)-benzamide 
• 134720-30-2 (E)-3,N-Diphenyl-N-(pyrrolidine-1-carbothioyl)-acrylamide 
• 134720-34-6 3,4-Dimethoxy-N-phenyl-N-(pyrrolidine-1-carbothioyl)-benzamide 
• 57962-59-1 N-phenyl-1-pyrrolidinethiocarboximidic acid methyl ester 
• 1279624-51-9 (1,2-bis(diphenylphosphinoethane))Ni(PhNC(S)N(CH₂)4)(BPh₄) 
• 1421761-34-3 C₂₂H₂₆N₄S 
• 19983-29-0 2-(pyrrolidin-1-yl)benzo[d]thiazole 
• 1392837-02-3 N-(1-iminoethyl)-N-phenylpyrrolidine-1-carbothioamide hydrobromide 
• 1312937-87-3 N-(benzenesulfonyl)-N'-phenylpyrrolidine-1-carboximidamide 

Relevant academic research and scientific papers

Development of Thiourea-Based Ligands for the Palladium-Catalyzed Bis(methoxycarbonylation) of Terminal Olefins

Thiourea-based ligands were evaluated for the palladium-catalyzed bis(methoxycarbonylation) of terminal olefins. The usefulness of these ligands for this reaction is demonstrated by their stability to oxidizing agents, and their superiority in preventing

Method for preparing aryl isothiourea

The invention discloses a method for preparing aryl isothiourea, wherein hydride is suspended in a solvent, and thiourea is sequentially added. O diiodo benzene followed by reaction to prepare aryl isothiosemicarbazone. The isothiourea structure is widely

2-Picolylamino(diphenylphosphinoselenoic)amide supported zinc complexes: Efficient catalyst for insertion of N–H bond into carbodiimides, isocyanates, and isothiocyanate

We report here the hydroamination of heterocumulenes such as carbodiimides, isocyanates, and isothiocyanates by zinc complexes supported by the ligand 2-picolylamino-(diphenylphosphinoselenoic)amide [{(Ph2P-(?Se)}2NCH2(C5H4N)] (1). A series of zinc complexes [κ2-{(Ph2P-(?Se)}2NCH2(C5H4N)ZnX2] [(X?Cl (2), Br (3a), I (4)] were prepared from ligand 1 and the corresponding zinc dihalide in a 1:1 molar ratio at 60°C in a chloroform solvent. The reaction of ligand 1 and ZnBr2 in methanol yielded another zinc complex [κ2-{(Ph2P-(?Se)}2NCH2(C5H4N)ZnBr2(CH3OH)] (3b). The molecular structures of compounds 3a, 3b, and 4 were established through single-crystal X-ray diffraction analyses. The solid-state structures of all the complexes revealed a κ2- chelation through pyridine nitrogen and selenium atoms of ligand 1 to the zinc ion. Complex 2 proved to be a competent pre-catalyst for the addition of the amine N–H bond to carbodiimides, isocyanates, and isothiocyanates. The reaction scope was expanded to reactions of aliphatic and aromatic amines with phenylisocyanate and phenylisothiocyanate in toluene solvents, which proceeded rapidly at room temperature with 5 mol% catalyst loading to yield (up to 99%) the corresponding derivatives of urea and thio-urea. However, a temperature of 90°C was needed for the hydroamination of N,N′ dicyclohexylcarbodiimide. We also report the most plausible mechanism of the hydroamination reaction.

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.

Hydroamination of carbodiimides, isocyanates, and isothiocyanates by a bis(phosphinoselenoic amide) supported titanium(IV) complex

The hydroamination of heterocumulenes such as carbodiimides, isocyanates, and isothiocyanates by a bis(phosphinoselenoic amide) supported titanium(iv) complex as a precatalyst is reported here. The titanium(iv) complex [{Ph2P(Se)NCH2CH2NPPh2(Se)}Ti(NMe2)2] (1) was synthesised by the reaction of tetrakis-(dimethylamido)titanium(iv) [Ti(NMe2)4] with [{Ph2P(Se)NHCH2CH2NHPPh2(Se)}] in toluene at ambient temperature. Titanium complex 1 proved to be a competent pre-catalyst for the addition of an amine N-H bond to carbodiimides, isocyanates, and isothiocyanates. The reaction scope was expanded to reactions of aliphatic and aromatic amines with phenylisocyanates and phenylisothiocyanates in toluene solvents proceeding rapidly at room temperature with 5 mol% catalyst loadings to yield the corresponding urea and thio-urea derivatives up to 99%. However, ambient temperature was needed for hydroamination of 1,3-dicyclohexylcarbodiimide. The amine addition reactions with isocyanates showed first order kinetics with respect to catalyst 1 as well as substrates. The most plausible mechanism for the hydroamination reaction was established by isolating 1,1-dimethylphenyl urea as a side product.

Efficient pyrrolidine catalyzed cycloaddition of aziridines with isothiocyanates, isoselenocyanates and carbon disulfide "on water"

The cycloaddition of aziridines with isothiocyanates, isoselenocyanates and carbon disulfide has been described using pyrrolidine as catalyst on water at moderate temperature. This protocol features the use of commercial amine as catalyst and water as sol

Water promoted one pot three-component synthesis of tetrazoles

A one pot, three component synthesis of tetrazoles via thiourea has been accomplished in water. Water enhances the solubility of a higher number of components in the three component protocol thus promoting the reaction. The synthesis involves a chemoselective exocyclic reaction, regioselective electrocyclisation and a preferred conformational orientation of the tetrazole side chain which are rationalised based on the relative magnitude of Garbisch angle strain/allylic strains anticipated during the course of the reaction.

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.

Nickel(II) complexes of di- and tri-substituted thiourea mono- and di-anions

Reaction of nickel(II) acetate, 1,2-bis(diphenylphosphino)ethane (dppe), and a di- or tri-substituted thiourea R1NHC(S)R2R 3 (R3 = H or alkyl) with trimethylamine in hot methanol gave cationic nickel(II) complex