Pyrithyldione

Base Information

• Chemical Name: Pyrithyldione
• CAS No.: 77-04-3
• Molecular Formula: C9H13 N O2
• Molecular Weight: 167.208
• European Community (EC) Number: 201-000-5
• NSC Number: 758237,89733
• UNII: 8AB20823CK
• DSSTox Substance ID: DTXSID4045262
• Nikkaji Number: J22.049C
• Wikipedia: Pyrithyldione
• Wikidata: Q408959
• NCI Thesaurus Code: C80677
• Metabolomics Workbench ID: 154149
• ChEMBL ID: CHEMBL1722501
• Mol file: 77-04-3.mol

Synonyms:3,3-diethyl-1,2,3,4-tetrahydro-2,4-pyridinedione;benedorm;didropyridine;Persedon;pyrithyldione

Chemical Property of Pyrithyldione

Chemical Property:

• Vapor Pressure: 0.000169mmHg at 25°C
• Melting Point: 92-93°; mp 97-98°; mp 81-86° [Scheibl, Wachter, Arch. Toxikol. 18, 253 (1960)]
• Refractive Index: 1.4680 (estimate)
• Boiling Point: 187-189 °C (14 mmHg)
• PKA: 11.69±0.40(Predicted)
• Flash Point: 147.8°C
• PSA: 46.17000
• Density: 1.029g/cm³
• LogP: 1.33420
• Storage Temp.: Room Temperature
• Solubility.: Dichloromethane; Ethyl Acetate; Methanol
• XLogP3: 1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 167.094628657
• Heavy Atom Count: 12
• Complexity: 239

Purity/Quality:

99% ^*data from raw suppliers

Pyridione ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn:Harmful
• Statements: R20/21:Harmful by inhalation and in contact with skin.
• Safety Statements: S23:Do not inhale gas/fumes/vapour/spray.

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1(C(=O)C=CNC1=O)CC
• Uses: hypnotic, sedative Pyridione is an intermediate in the synthesis of Methyprylon (M338670), which is a sedative/hypnotic drug used for treating insomnia.

Technology Process of Pyrithyldione

There total 4 articles about Pyrithyldione 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:

triphenylmethyl pyrithyldione → 3,3-diethyl-2,4(1H,3H)-pyridinedione (77-04-3)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; water; at 20 ℃;

DOI:10.1016/S0040-4039(02)01964-0

Reference yield:

2,2-diethyl-5-amino-3-oxo-pent-4-enoic acid ethyl ester (74367-91-2) → 3,3-diethyl-2,4(1H,3H)-pyridinedione (77-04-3)

Guidance literature:

With ethanol; sodium ethanolate;

Reference yield:

ethyl 2,2-diethyl-3-oxobutanoate (1619-57-4) → 3,3-diethyl-2,4(1H,3H)-pyridinedione (77-04-3)

Guidance literature:

Multi-step reaction with 2 steps

1: absolute ethanol / 150 - 155 °C

2: ethanol; sodium ethylate

With ethanol; sodium ethanolate;

upstream raw materials:

2,2-diethyl-5-amino-3-oxo-pent-4-enoic acid ethyl ester

ethyl 2,2-diethyl-3-oxobutanoate

Downstream raw materials:

3,3-diethyl-5-hydroxymethyl-1H-pyridine-2,4-dione

3,3-diethyl-6-benzyl-piperidine-2,4-dione

3,3-diethyl-6-phenyl-piperidine-2,4-dione

N-Methyl-2,4-dioxo-3,3-diethyl-1,2,3,4-tetrahydropyridin

Refernces