Proline thiohydantoin

Base Information

• Chemical Name: Proline thiohydantoin
• CAS No.: 61160-12-1
• Molecular Formula: C₆H₈N₂OS
• Molecular Weight: 156.208
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID40976674
• Wikidata: Q82961629
• Mol file: 61160-12-1.mol

Synonyms:proline thiohydantoin

Chemical Property of Proline thiohydantoin

Chemical Property:

• Boiling Point: °Cat760mmHg
• PKA: 11.04±0.20(Predicted)
• Flash Point: °C
• PSA: 67.92000
• Density: 1.44g/cm³
• LogP: 0.07930
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 156.03573406
• Heavy Atom Count: 10
• Complexity: 204

Purity/Quality:

(7aS)-hexahydro-3-thioxo-1H-Pyrrolo[1,2-c]imidazol-1-one 97.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC2C(=O)NC(=S)N2C1
• Isomeric SMILES: C1C[C@H]2C(=O)NC(=S)N2C1

Technology Process of Proline thiohydantoin

There total 6 articles about Proline thiohydantoin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

thiourea (17356-08-0) + L-proline (147-85-3,25191-13-3,37159-97-0,4305-67-3,4607-28-7) → 3-thioxohexahydropyrrolo<1,2-c>imidazol-1-one (61160-12-1)

Guidance literature:

for 0.5h; Heating;

DOI:10.3390/11100739

Reference yield: 82.0%

N-cyanoproline methyl ester (367906-67-0) → 3-thioxohexahydro-1H-pyrrolo[1,2-c]imidazol-1-one (61160-12-1,32085-78-2)

Guidance literature:

With Thiophosphorsaeure-O,O-diethylester; at 60 ℃; for 1h; Neat (no solvent);

DOI:10.1016/j.tetlet.2012.02.087

Reference yield: 62.0%

thiourea (17356-08-0) + rac-Pro-OH (609-36-9,25191-13-3,37159-97-0,4305-67-3,4607-28-7) → 3-thioxohexahydro-1H-pyrrolo[1,2-c]imidazol-1-one (61160-12-1,32085-78-2)

Guidance literature:

at 180 - 195 ℃; for 1.25h;

DOI:10.1002/anie.201501275

upstream raw materials:

Benzoyl isothiocyanate

ethyl (2S)-pyrrolidine-2-carboxylate

ammonium thiocyanate

acetic anhydride

Refernces

• 1、 Bispo, Marcelle de Lima Ferreira,Garbin, Renata Perugini Biasi,Macedo, Fernando,Nakazato, Gerson,Ogatta, Sueli Fumie Yamada,Ribeiro, Jhonatan Macedo,de Carvalho, Priscila Goes Camargo,de Fátima, ?ngelo. "Synthesis and antimicrobial activity of thiohydantoins obtained from L-amino acids". . p. 94 - 102. Retrieved 2020/02/06.
• 2、 Kumar, Vinod,Rana, Hemlata,Sankolli, Ravish,Kaushik. "Novel and efficient protocol for the syntheses of N-1 substituted thiohydantoin and a bicyclothiohydantoin under solvent-free conditions". experimental part. p. 2377 - 2379. Retrieved 2012/05/31.