5-Oxo-5H-thiazolo[3,2-A]pyrimidine-6-carbonyl chloride

Base Information

• Chemical Name: 5-Oxo-5H-thiazolo[3,2-A]pyrimidine-6-carbonyl chloride
• CAS No.: 76661-92-2
• Molecular Formula: C7H3 Cl N2 O2 S
• Molecular Weight: 214.62892
• Hs Code.: 2934100090
• DSSTox Substance ID: DTXSID30546188
• Wikidata: Q82423942
• Mol file: 76661-92-2.mol

Synonyms:76661-92-2;5-OXO-5H-THIAZOLO[3,2-A]PYRIMIDINE-6-CARBONYL CHLORIDE;DTXSID30546188;5-Oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carbonyl chloride;5-OXO-5H-THIAZOLO[3,2-A]PYRIMIDINE-6-CARBONYLCHLORIDE

Chemical Property of 5-Oxo-5H-thiazolo[3,2-A]pyrimidine-6-carbonyl chloride

Chemical Property:

• PSA: 79.68000
• LogP: 1.13500
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 213.9603762
• Heavy Atom Count: 13
• Complexity: 386

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CSC2=NC=C(C(=O)N21)C(=O)Cl

Technology Process of 5-Oxo-5H-thiazolo[3,2-A]pyrimidine-6-carbonyl chloride

There total 2 articles about 5-Oxo-5H-thiazolo[3,2-A]pyrimidine-6-carbonyl chloride 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:

6-Carboxy-5(H)-oxothiazolo<3,2-a>pyrimidine (51991-94-7) → 5-Oxo-5H-thiazolo[3,2-a]pyrimidine-6-carbonyl chloride (76661-92-2)

Guidance literature:

With thionyl chloride; for 4h; Heating;

Reference yield:

6-ethoxycarbonyl-5-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine (32278-52-7) → 5-Oxo-5H-thiazolo[3,2-a]pyrimidine-6-carbonyl chloride (76661-92-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / 2 M aq. NaOH / ethanol / 3 h / 20 °C

2: oxalyl chloride; DMF / CH₂Cl₂ / 1.83 h / 0 - 20 °C

With sodium hydroxide; oxalyl dichloride; N,N-dimethyl-formamide; In ethanol; dichloromethane; 1: Hydrolysis / 2: Chlorination;

DOI:10.1002/jhet.5570370115

Reference yield: 61.0%

5-Oxo-5H-thiazolo[3,2-a]pyrimidine-6-carbonyl chloride (76661-92-2) + aniline (62-53-3) → 5-oxo-N-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxamide

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 20h;

DOI:10.1002/jhet.5570370115

upstream raw materials:

6-Carboxy-5(H)-oxothiazolo<3,2-a>pyrimidine

6-ethoxycarbonyl-5-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine

Downstream raw materials:

5-oxo-N-(1,3-thiazol-2-yl)-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxamide

Refernces

• 1、 Shridhar, D. R.,Jogibhukta, M.,Krishnan, V. S. H.. "Synthesis and Anthelmintic Activity of Some Carbamates, Thiocarbamates and Ureas Derived from 6-Carboxy-5(H)-oxothiazolopyrimidine". . p. 345 - 346. Retrieved 2007/10/02.