Sodium Bicarbonate → HCID 117760882, compound

HRID 523209Notes

Reaction equation

HRID 523209 reaction equation
[NH2:1][C:2]1[CH:18]=[CH:17][CH:16]=[CH:15][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([Br:13])[C:8]=1[CH3:14])=[O:5].[C:19]([O-])(O)=[O:20].[Na+]>C1COCC1>[Br:13][C:9]1[C:8]([CH3:14])=[C:7]([N:6]2[C:4](=[O:5])[C:3]3[C:2](=[CH:18][CH:17]=[CH:16][CH:15]=3)[NH:1][C:19]2=[O:20])[CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 103821981HCID 103821981, compound

Product 1

HCID 117760882HCID 117760882, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-amino-N-(3-bromo-2-methylphenyl)benzamide (2.00 g, 6.55 mmol) in THF (50 mL) was treated with bis(trichloromethyl)carbonate[triphosgene] (2.92 g, 9.83 mmol) and heated at reflux for 60 min. The cooled mixture was treated with saturated aqueous NaHCO3, extracted with EtOAc, and the combined organic phases were washed twice with saturated NaHCO3, then with water, dried and concentrated. The residue was triturated with DCM to give a white solid which was collected by filtration. The residue from concentration of the filtrate was triturated with DCM to give additional white solid which was collected by filtration. The two solids were combined to give 3-(3-bromo-2-methylphenyl)quinazoline-2,4(1H,3H)-dione as a white solid (2.10 g, 97% yield). Mass spectrum m/z 331, 333 (M+H)+. 1H NMR (400 MHz, MeOH-d4) δ 8.07 (dd, J=7.92, 1.32 Hz, 1H), 7.65-7.75 (m, 2H), 7.21-7.32 (m, 4H), 2.20 (s, 3H). 1H NMR (400 MHz, chloroform-d) δ 9.38 (br. s., 1H), 8.19 (dd, J=7.9, 1.1 Hz, 1H), 7.76-7.69 (m, 1H), 7.69-7.60 (m, 1H), 7.35-7.17 (m, 3H), 7.04-6.97 (m, 1H), 2.28 (s, 3H).

Workup

  1. temperatureheated
  2. temperatureat reflux for 60 min
  3. extractionextracted with EtOAc
  4. washthe combined organic phases were washed twice with saturated NaHCO3
  5. dry with materialwith water, dried
  6. concentrationconcentrated
  7. customThe residue was triturated with DCM
  8. customto give a white solid which
  9. filtrationwas collected by filtration
  10. customThe residue from concentration of the filtrate was triturated with DCM
  11. customto give additional white solid which
  12. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-9fbc77a1562b46b1a7ddce694c99a86e
Source dataset
uspto-grants-2016_05
Patent number
US09334290B2

Reaction notes

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