6,7-Dimethoxyquinazoline-2,4-dione

Base Information

• Chemical Name: 6,7-Dimethoxyquinazoline-2,4-dione
• CAS No.: 28888-44-0
• Molecular Formula: C10H10N2O4
• Molecular Weight: 222.2
• Hs Code.: 29339990
• European Community (EC) Number: 249-288-1
• UNII: K7867Z125J
• DSSTox Substance ID: DTXSID9046100
• Nikkaji Number: J92.427J
• Wikidata: Q27282043
• ChEMBL ID: CHEMBL1403860
• Mol file: 28888-44-0.mol

Synonyms:2,5-Dihydroxy-6,7-dimethoxyquinazoline;6,7-Dimethoxy-1H-quinazoline-2,4-dione;6,7-Dimethoxy-2,4(1H,3H)-quinazolinedione;6,7-Dimethoxyquinazoline-2,4-diol;

Chemical Property of 6,7-Dimethoxyquinazoline-2,4-dione

Chemical Property:

• Appearance/Colour: brown powder
• Melting Point: 323 °C
• Refractive Index: 1.552
• Boiling Point: 363.37°C (rough estimate)
• PKA: 10.27±0.20(Predicted)
• PSA: 84.18000
• Density: 1.312 g/cm³
• LogP: 0.23360
• Storage Temp.: 2-8°C
• Solubility.: Aqueous Acid (Sparingly)
• Water Solubility.: insoluble
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 222.06405680
• Heavy Atom Count: 16
• Complexity: 307

Purity/Quality:

99% ^*data from raw suppliers

6,7-Dimethoxyquinazoline-2,4-dione ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C2C(=C1)C(=O)NC(=O)N2)OC
• Uses: An intermediate in the preparation of Alfuzosin hydrochloride (A532000), an antihypertensive. 6,7-Dimethoxyquinazoline-2,4-dione (Doxazosin EP Impurity D) is an intermediate in the preparation of Alfuzosin hydrochloride (A532000), an antihypertensive.

Technology Process of 6,7-Dimethoxyquinazoline-2,4-dione

There total 20 articles about 6,7-Dimethoxyquinazoline-2,4-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: 100.0%

carbon dioxide (124-38-9,18923-20-1) + 2-amino-4,5-dimethoxybenzonitrile (26961-27-3) → 6,7-dimethoxy-1H-quinazoline-2,4-dione (28888-44-0)

Guidance literature:

With 2,6-dichloro-benzonitrile; at 120 ℃; for 4h; under 750.075 Torr;

DOI:10.1055/s-2007-983808

Reference yield: 99.1%

2-amino-4,5-dimethoxybenzonitrile (26961-27-3) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → 6,7-dimethoxy-1H-quinazoline-2,4-dione (28888-44-0)

Guidance literature:

With carbon dioxide; In water; at 150 ℃; for 5h; under 37503.8 Torr;

DOI:10.1021/acs.oprd.6b00244

Reference yield: 97.0%

2-Amino-4,5-dimethoxybenzoic acid (5653-40-7) → 6,7-dimethoxy-1H-quinazoline-2,4-dione (28888-44-0)

Guidance literature:

With acetic acid; In water; at 35 ℃; for 0.5h;

DOI:10.1021/jo026217o

upstream raw materials:

4,5-dimethoxy-2-ureido-benzoic acid

potassium cyanate

2-Amino-4,5-dimethoxybenzoic acid

carbon dioxide

Downstream raw materials:

2-chloro-6,7-dimethoxy-3H-quinazolin-4-one

4-(3-carboxyanilino)-2-chloro-6,7-dimethoxyquinazo line

Refernces

• 1、 Phatake, Vishal V.,Gokhale, Tejas A.,Bhanage, Bhalchandra M.. "[TBDH][HFIP] ionic liquid catalyzed synthesis of quinazoline-2,4(1H,3H)-diones in the presence of ambient temperature and pressure". . . Retrieved 2021/07/28.
• 2、 Huang, Min-Min,Sheng, Zhi-Zheng,Wu, Hai-Hong,Xia, Fei,Xue, Teng. "Alcohol amine-catalyzed CO2conversion for the synthesis of quinazoline-2,4-(1H,3H)-dione in water". . p. 34910 - 34915. Retrieved 2020/10/12.