Tetrahydro-2-methyl-3-thioxo-1,2,4-triazine-5,6-dione

Base Information

• Chemical Name: Tetrahydro-2-methyl-3-thioxo-1,2,4-triazine-5,6-dione
• CAS No.: 58909-39-0
• Molecular Formula: C4H5N3O2S
• Molecular Weight: 159.169
• Hs Code.: 29336990
• European Community (EC) Number: 261-490-1
• UNII: 679WF9Q9W1
• DSSTox Substance ID: DTXSID60207654
• Nikkaji Number: J261.953I
• Wikidata: Q27264105
• Mol file: 58909-39-0.mol

Synonyms:58909-39-0;Thiotriazinone;Tetrahydro-2-methyl-3-thioxo-1,2,4-triazine-5,6-dione;2-methyl-3-thioxo-1,2,4-triazinane-5,6-dione;1,2,4-Triazin-2-methyl-6-hydroxy-3-thio-5-one;2-Methyl-3-sulfanyl-1,2-dihydro-1,2,4-triazine-5,6-dione;2-methyl-3-sulfanylidene-1,2,4-triazinane-5,6-dione;UNII-679WF9Q9W1;679WF9Q9W1;EINECS 261-490-1;1,2,4-Triazine-5,6-dione, tetrahydro-2-methyl-3-thioxo-;1,2,4-Triazine-2-methyl-6-hydroxy-3-thio-5-one;2,5-Dihydro-6-Hydroxy-3-Mercapto-2-Methyl-5-Oxo-1,2,4-Triazine;Ceftriaxone Impurity C;Ro 11-8390;MLS006010407;SCHEMBL4608486;6-hydroxy-3-mercapto-2-methyl-1,2,4-triazin-5(2H)-one;DTXSID60207654;UMWWHOXOVPIGFD-UHFFFAOYSA-N;2-Methyl-5,6-dioxo-1,2,5,6-tetrahydro-1,2,4-triazine-3-thiol;MFCD00185756;AKOS006228121;AKOS015961510;AKOS025312531;CS-T-62035;SB73223;AC-13903;AS-11758;SMR004701407;CEFTRIAXONE SODIUM IMPURITY F [IP];CS-0151199;FT-0610373;EN300-92093;SR-01000944806;2-methyl-3-sulfanyl-1H-1,2,4-triazine-5,6-dione;CEFTRIAXONE SODIUM IMPURITY C [EP IMPURITY];J-509964;SR-01000944806-1;6-hydroxy-3-mercapto-2-methyl-5-oxo-1,2,4-triazine;BRD-K15365721-001-01-1;Q27264105;2-Methyl-3-mercapto-1,2,4-triazine-5,6(1H,2H)-dione;Tetrahydro-2-methyl-3-thioxo-1,2,4-triazine-5,6-dione, 97%;1,2,3,4-Tetrahydro-2-methyl-3-thioxo-1,2,4-triazine-5,6-dione;1,2,3,4-Tetrahydro-2-methyl-3-thioxo-1,2,4-triazine-5.6-dione;2-methyl-3-mercapto-5-oxo-6-hydroxy-2,5-dihydro-1,2,4-triazine;2-methyl-3-mercapto-6-hydroxy-2,5-dihydro-1,2,4-triazin-5-one;6-hydroxy-2-methyl-3-thioxo-3,4-dihydro-1,2,4-triazin-5(2H)-one

Chemical Property of Tetrahydro-2-methyl-3-thioxo-1,2,4-triazine-5,6-dione

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 0.000795mmHg at 25°C
• Melting Point: 168-171 °C(lit.)
• Refractive Index: 1.678
• Boiling Point: 272.3 °C at 760 mmHg
• PKA: 5.34±0.20(Predicted)
• Flash Point: 118.5 °C
• PSA: 102.74000
• Density: 1.62 g/cm³
• LogP: -0.86880
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Sparingly), Methanol (Slightly)
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 159.01024758
• Heavy Atom Count: 10
• Complexity: 215

Purity/Quality:

99% ^*data from raw suppliers

Thiotriazinone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 20/21/22-36
• Safety Statements: 36-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C(=S)NC(=O)C(=O)N1
• Uses: Reagent used in the preparation of Cefalosporins. Thiotriazinone can be used in the preparation of Cefalosporins.

Technology Process of Tetrahydro-2-methyl-3-thioxo-1,2,4-triazine-5,6-dione

There total 6 articles about Tetrahydro-2-methyl-3-thioxo-1,2,4-triazine-5,6-dione 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: 92.7%

2-methyl-thiosemicarbazide (6938-68-7) + oxalic acid diethyl ester (95-92-1) → 2-methyl-3-mercapto-5-oxo-6-hydroxy-2,5-dihydro-1,2,4-triazine (58909-39-0)

Guidance literature:

With dmap; N,N,N,N,-tetramethylethylenediamine; sodium methylate; In methanol; ethanol; at 15 - 55 ℃; for 4h; Temperature; Solvent; Reagent/catalyst;

Reference yield: 75.0%

Dimethyl oxalate (553-90-2) + ammonium thiocyanate + methylhydrazine (60-34-4) → 2-methyl-3-mercapto-5-oxo-6-hydroxy-2,5-dihydro-1,2,4-triazine (58909-39-0)

Guidance literature:

ammonium thiocyanate; methylhydrazine; In water; at 95 - 100 ℃;

Dimethyl oxalate; With sodium methylate; In methanol; at 65 - 75 ℃; for 6h; Temperature;

Reference yield:

sodium salt of ceftriaxone → 2-methyl-3-mercapto-5-oxo-6-hydroxy-2,5-dihydro-1,2,4-triazine (58909-39-0) + (6R,7S)-7-{2-(2-Amino-thiazol-4-yl)-2-[(Z)-methoxyimino]-acetylamino}-3-(6-hydroxy-2-methyl-5-oxo-2,5-dihydro-[1,2,4]triazin-3-ylsulfanylmethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid anion + C14H13N5O6S2(2-) (153470-19-0)

Guidance literature:

With Carbonate buffer; at 37 ℃; Rate constant; H/D-isotopic effect were studied too;

DOI:10.1002/hlca.19930760805

upstream raw materials:

2-methyl-thiosemicarbazide

oxalic acid diethyl ester

Dimethyl oxalate

methylhydrazine

Downstream raw materials:

ceftriaxone

tetrahydro-2-methyl-5,6-dioxo-3-thioxo-as-triazine-1(2H)-carboxylic acid benzyl ester

7-aminoceftrizine

7-amino-3-[(2,5-dihydro-6-hydroxy-2-methyl-5-oxo-1,2,4-triazine-3-mercapto)methyl]-3 cephalosporin-4-carboxylic acid

Refernces

• 1、 -. "Tricyclic synthesis process of triazine". Paragraph 0024-0031. . Retrieved 2019/04/06.
• 2、 Vilanova,Munoz,Donoso,Garcia Blanco. "HPLC and 1H-NMR studies of alkaline hydrolysis of some 7-(oxyiminoacyl)cephalosporins". . p. 2789 - 2802. Retrieved 2007/10/02.