6-Chloroquinazoline-2,4(1H,3H)-dione

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.General procedure: 2-aminobenzonitrile (1 mmol) and KCC-1/STPP NPs (0.7 mg) were mixed together. The autoclave was closed, purged twice with CO2 gas, pressurized to 1.5 MPa of CO2, and heated at 70°C for 50 min. Then, the reactor was cooled to ambient temperature and the resulting mixture was transferred to a 50 mL round-bottom flask. During completion, the reaction progress was monitored by TLC. Following its completion, EtOH was added to the reaction mixture and the catalyst was separated by filtration. Afterwards, the solvent was removed from the solution under reduced pressure and the resulting product was purified by recrystallization using n-hexane/ethyl acetate. The products are known and their sample characterization data is presented in the Supplemental Materials.Weigh 0.763 g (5 mmol) of 2-amino-5-chlorobenzonitrile was placed in a polytetrafluoroethylene liner of a stainless steel reactor, and3 mL of a diethanolamine aqueous solution having a concentration of 1.33 mol / L was added and stirred for 2 minutes , The carbon dioxide was heated and the temperature was raisedto 100 ° C, and the carbon dioxide pressure was adjusted to 1 MPa for the carboxylation reaction under stable conditions for 12 hours.Antiupon end, the reaction system was cooled to room temperature slowly released unreacted carbon dioxide, was added 10mL of deionized water and stirreddispersion product, resulting precipitate was filtered and washed with a small amount of distilled water, and then 15mL / wash three times with methyl tert-butyl ether Andthe product was dried at a temperature of 100 ° C to give 6-chloroquinazoline-2, 4 (1H, 3H) -dione having a yield of 93percent.General procedure: 2-aminobenzonitrile (1mmol), and KCC-1/IL NPs (0.0007g) were added. The autoclave was closed, purged twice with COIn anhydrous, anaerobic, argon protection, 0.0999 g (7.5 x 10-5 mol) of {L2Eu [N (SiMe3) 2] THF} 2 was added to the reaction flask, An additional 11.2 μL (7.5 × 10 -5 mol) DBU was added, under the protection of carbon dioxide bag, Add 2 mL of dimethyl sulfoxide, add 0.2949 g (1.5 × 10 -3 mol) of 2-amino-5-chlorobenzonitrile, The reaction was stirred in a constant temperature bath at 100 ° C. After 24h, add 5mL 2mol / L hydrochloric acid to quench the reaction, Suction filtration, successively washed with 3 × 5mL hydrochloric acid, toluene and ether solids, the residual solvent was stripped, dried solids, The product was obtained in 91percent yield.Step 1 A 250 mL round bottom flask was charged with 2-amino-5- chlorobenzoic acid (17.2 g, 0.1 mol) and urea (30 g, 0.5 mol). The resulting mixture was heated to 200 °C for 3 h. Work up: the reaction mixture was washed by water and filtered. The solid was dried to give 18.5 g (94percent) of the product. MS m/z: 196 (M+HGeneral procedure: A mixture of 2-aminobenzoic acid 3a (2.00 g, 14.91 mmol), urea (4.40 g, 73.26 mmol) in phenol (6.00 g, 63.76 mmol) was heated at 150 Cunder the reflux for 10 h. The reaction mixture was cooled downto 100 C and ethanol/water (1:1) 10 mL was added drop-wise.The reaction mixture was cooled to rt, filtered, washed with ethanol(5 mL), and dried to afford 4a in 53percent yield (1.26 g).Part B: Into a 500-mL 3-necked round-bottom flask, was placed a solution of 2-ammo-5-chlorobenzoic acid (10 g, 58 48 mmol, 1 00 equiv) in water (100 mL), acetic acid (8 g, 133 33 mmol, 2 24 equiv) This was followed by the addition of NaOCN (8 2 g, 126 15 mmol, 2 13 equiv) The mixture was stirred for 30 rains at 3OGeneral 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.General procedure: 2-aminobenzonitrile (1 mmol) and KCC-1/STPP NPs (0.7 mg) were mixed together. The autoclave was closed, purged twice with CO2 gas, pressurized to 1.5 MPa of CO2, and heated at 70°C for 50 min. Then, the reactor was cooled to ambient temperature and the resulting mixture was transferred to a 50 mL round-bottom flask. During completion, the reaction progress was monitored by TLC. Following its completion, EtOH was added to the reaction mixture and the catalyst was separated by filtration. Afterwards, the solvent was removed from the solution under reduced pressure and the resulting product was purified by recrystallization using n-hexane/ethyl acetate. The products are known and their sample characterization data is presented in the Supplemental Materials.Weigh 0.763 g (5 mmol) of 2-amino-5-chlorobenzonitrile was placed in a polytetrafluoroethylene liner of a stainless steel reactor, and3 mL of a diethanolamine aqueous solution having a concentration of 1.33 mol / L was added and stirred for 2 minutes , The carbon dioxide was heated and the temperature was raisedto 100 ° C, and the carbon dioxide pressure was adjusted to 1 MPa for the carboxylation reaction under stable conditions for 12 hours.Antiupon end, the reaction system was cooled to room temperature slowly released unreacted carbon dioxide, was added 10mL of deionized water and stirreddispersion product, resulting precipitate was filtered and washed with a small amount of distilled water, and then 15mL / wash three times with methyl tert-butyl ether Andthe product was dried at a temperature of 100 ° C to give 6-chloroquinazoline-2, 4 (1H, 3H) -dione having a yield of 93percent.General procedure: 2-aminobenzonitrile (1mmol), and KCC-1/IL NPs (0.0007g) were added. The autoclave was closed, purged twice with COIn anhydrous, anaerobic, argon protection, 0.0999 g (7.5 x 10-5 mol) of {L2Eu [N (SiMe3) 2] THF} 2 was added to the reaction flask, An additional 11.2 μL (7.5 × 10 -5 mol) DBU was added, under the protection of carbon dioxide bag, Add 2 mL of dimethyl sulfoxide, add 0.2949 g (1.5 × 10 -3 mol) of 2-amino-5-chlorobenzonitrile, The reaction was stirred in a constant temperature bath at 100 ° C. After 24h, add 5mL 2mol / L hydrochloric acid to quench the reaction, Suction filtration, successively washed with 3 × 5mL hydrochloric acid, toluene and ether solids, the residual solvent was stripped, dried solids, The product was obtained in 91percent yield.Step 1 A 250 mL round bottom flask was charged with 2-amino-5- chlorobenzoic acid (17.2 g, 0.1 mol) and urea (30 g, 0.5 mol). The resulting mixture was heated to 200 °C for 3 h. Work up: the reaction mixture was washed by water and filtered. The solid was dried to give 18.5 g (94percent) of the product. MS m/z: 196 (M+HGeneral procedure: A mixture of 2-aminobenzoic acid 3a (2.00 g, 14.91 mmol), urea (4.40 g, 73.26 mmol) in phenol (6.00 g, 63.76 mmol) was heated at 150 Cunder the reflux for 10 h. The reaction mixture was cooled downto 100 C and ethanol/water (1:1) 10 mL was added drop-wise.The reaction mixture was cooled to rt, filtered, washed with ethanol(5 mL), and dried to afford 4a in 53percent yield (1.26 g).Part B: Into a 500-mL 3-necked round-bottom flask, was placed a solution of 2-ammo-5-chlorobenzoic acid (10 g, 58 48 mmol, 1 00 equiv) in water (100 mL), acetic acid (8 g, 133 33 mmol, 2 24 equiv) This was followed by the addition of NaOCN (8 2 g, 126 15 mmol, 2 13 equiv) The mixture was stirred for 30 rains at 3O

Molecular Weight:196.59
XLogP3:1.4
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Exact Mass:196.0039551
Monoisotopic Mass:196.0039551
Topological Polar Surface Area:58.2
Heavy Atom Count:13
Complexity:257
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes