ChemicalBook CAS DataBase List 2,4(1H,3H)-Quinazolinedione, 6-methyl-

2,4(1H,3H)-Quinazolinedione, 6-methyl- synthesis

7synthesis methods

Product Name:2,4(1H,3H)-Quinazolinedione, 6-methyl-
CAS Number:62484-16-6
Molecular formula:C9H8N2O2
Molecular Weight:176.17

5925-93-9 Synthesis

5925-93-9
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$13.00/250mg

124-38-9
129 suppliers
$175.00/23402

62484-16-6
72 suppliers
$13.00/100mg

Yield: 99%

Reaction Conditions:

with tetrabutyl ammonium fluoride in dimethyl sulfoxide at 110; under 15001.5 Torr; for 24 h;Autoclave;

Steps:

4.4. Synthesis of quinazoline-2,4(1H,3H)-diones 5 from 2-aminobenzonitriles 4 and CO2: general procedure
General procedure: Table 5: To a DMSO-d6 solution (1 mL) of 2-aminobenzonitrile 4a (1 mmol) in a stainless steel autoclave was added a catalyst (0.01 mmol) under an argon atmosphere. The autoclave was sealed, heated at 110°C and then pressurized with CO2 of 2 MPa. The cyclization reaction of 4a proceeded by the magnetic stirring of the resulting mixture at 110°C for 3 h. After the reaction the autoclave was cooled in an ice bath and depressurized. The chemical yield of quinazoline-2,4(1H,3H)-dione 5a was determined by integrating 1HNMR with reference to an internal standard (3,5-dimethoxybenzylalcohol), which was added to the reaction mixture. Table 6: DMSO solution (6 mL) of 4 (6 mmol) was treated for the carboxylative cyclization of 4 with CO2 according to the procedure of Table 5. After the reaction, the autoclave was cooled in an ice bath and depressurized, and the reaction mixture was added to water (60 mL). The precipitation was collected by filtration, washed with water and diethyl ether, and then dried in vacuo at 35°C for 15 h to give the pure product 5.

References:

Fujii, Akira;Matsuo, Hideaki;Choi, Jun-Chul;Fujitani, Tadahiro;Fujita, Ken-ichi [Tetrahedron,2018,vol. 74,# 24,p. 2914 - 2920]

590-28-3 Synthesis