* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Reference：
[1] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 1, p. 119 - 132
2
[ 635-21-2 ]
[ 75-05-8 ]
[ 7142-09-8 ]
Reference：
[1] Chemical Communications, 2017, vol. 53, # 31, p. 4362 - 4365
3
[ 635-21-2 ]
[ 7142-09-8 ]
Reference：
[1] Journal of Medicinal Chemistry, 1990, vol. 33, # 6, p. 1721 - 1728
[2] European Journal of Medicinal Chemistry, 2014, vol. 86, p. 613 - 627
[3] Patent: WO2015/19121, 2015, A1,
4
[ 57-13-6 ]
[ 635-21-2 ]
[ 1640-60-4 ]
Yield
Reaction Conditions
Operation in experiment
94%
at 200℃; for 3 h;
Step 1 6-Chloroquinazoline-2,4(1H,3H)-dione 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+H+).
94%
at 200℃; for 3 h;
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+H+)
79%
at 150℃; for 10 h;
General 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).
Reference：
[1] Patent: US2010/120741, 2010, A1, . Location in patent: Page/Page column 24
[2] Patent: WO2011/112731, 2011, A2, . Location in patent: Page/Page column 79
[3] Chemistry Letters, 2005, vol. 34, # 10, p. 1438 - 1439
[4] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 24, p. 7717 - 7727
[5] Journal of Medicinal Chemistry, 2010, vol. 53, # 6, p. 2390 - 2400
[6] Tetrahedron, 2012, vol. 68, # 43, p. 8908 - 8915
[7] Journal of Medicinal Chemistry, 2014, vol. 57, # 12, p. 5141 - 5156
[8] Chemical and Pharmaceutical Bulletin, 2015, vol. 63, # 2, p. 75 - 80
5
[ 917-61-3 ]
[ 635-21-2 ]
[ 1640-60-4 ]
Yield
Reaction Conditions
Operation in experiment
44%
Stage #1: With acetic acid In water at 30℃; for 0.5 h; Stage #2: With sodium hydroxide In water at 30℃; Stage #3: With hydrogenchloride In water
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 3O0C To this was added sodium hydroxide (86 g, 2 15 mol, 37 00 equiv) The resulting solution was stirred overnight at 30cC The solids were collected by filtration The residue was dissolved in water The pH value of the solution was adjusted to 7 with hydrogen chloπde (12 mol/L) The solids were collected by filtration This resulted in 5 g (44percent) of 6 chloroqmnazolme-2,4(lH,3H)-dione as a white solid.
Reference：
[1] Chemistry Letters, 2005, vol. 34, # 10, p. 1438 - 1439
[2] Chinese Chemical Letters, 2012, vol. 23, # 4, p. 431 - 433
[3] Journal of Chemical Research, 2007, # 6, p. 358 - 361
7
[ 635-21-2 ]
[ 1640-60-4 ]
Reference：
[1] Tetrahedron, 1997, vol. 53, # 25, p. 8457 - 8478
[2] Journal of the American Chemical Society, 1947, vol. 69, p. 940
[3] Patent: US5688803, 1997, A,
8
[ 635-21-2 ]
[ 162135-93-5 ]
Reference：
[1] Australian Journal of Chemistry, 1997, vol. 50, # 5, p. 473 - 478
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