Sodium Hydroxide → 3-(2-[1,3]dioxolan-2-yl-ethyl)-1H-quinazoline-2,4-dione

HRID 1266979Notes

Reaction equation

HRID 1266979 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11]([NH:13][CH2:14][CH2:15][CH:16]1[O:20][CH2:19][CH2:18][O:17]1)=[O:12].[OH-].[Na+]>C(O)C.O>[O:17]1[CH2:18][CH2:19][O:20][CH:16]1[CH2:15][CH2:14][N:13]1[C:3](=[O:2])[C:4]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:10][C:11]1=[O:12]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 697076212-[3-(2-[1,3]Dioxolan-2-yl-ethyl)-ureido]-benzoic acid methyl ester

Product 1

HCID 185451993-(2-[1,3]dioxolan-2-yl-ethyl)-1H-quinazoline-2,4-dioneYield 43%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A white mixture of 2-[3-(2-[1,3]dioxolan-2-yl-ethyl)-ureido]-benzoic acid methyl ester (0.50 g, 1.70 mmol) and 1N sodium hydroxide (2.0 mL) in ethanol (10 mL) was warmed until all the solids had gone into solution. The resulting colorless solution was cooled to ambient temperature and stirred for 30 minutes. Concentration yielded a colorless foam which was dissolved in water (15 mL); after 15 minutes, a white crystalline solid formed. The white crystalline solid was collected and dried to yield 3-(2-[1,3]dioxolan-2-yl-ethyl)-1H-quinazoline-2,4-dione (0.19 g, 43%). 1NMR CDCl3 δ7.92 (dd, J=1, 8 Hz, 1H), 7.67-7.61 (m, 1H), 7.22-7.15 (m, 2H) 4.88 (t, J=4 Hz, 1H), 4.00 (t, J=7 Hz, 2H), 3.89-3.71 (m, 4H), 1.93-1.86 (m, 2H).

Workup

  1. temperaturewas warmed until all the solids
  2. concentrationConcentration
  3. customyielded a colorless foam which
  4. waitafter 15 minutes
  5. customa white crystalline solid formed
  6. customThe white crystalline solid was collected
  7. customdried

Sources & evidence

ORD record
ord-9f9bf3947d2c48029c21affdf1c99217
Source dataset
uspto-grants-2003_04
Patent number
US06552015B2

Reaction notes

Loading…