Acetonitrile → HCID 178482429, compound

HRID 1783631Notes

Reaction equation

HRID 1783631 reaction equation
[C:1](#[N:3])C.[Br:4][C:5]1[CH:16]=[CH:15][C:8]2[NH:9][C:10](=O)[O:11][C:12](=O)[C:7]=2[CH:6]=1.C[NH:18]C(=N)SC.C(=O)([O-])[O-].[Na+].[Na+]>O>[Br:4][C:5]1[CH:6]=[C:7]2[C:8](=[CH:15][CH:16]=1)[NH:9][C:10]([NH:3][CH3:1])=[N:18][C:12]2=[O:11]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 10340Sodium CarbonateHCID 2885615-Bromoisatoic AnhydrideHCID 178485202HCID 178485202, compound

Product 1

HCID 178482429HCID 178482429, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a combined solution of acetonitrile (360 mL) and water (90 mL) was added 6-bromo-1H-benzo[d][1,3]oxazine-2,4-dione (24.2 g, 0.1 mol), 1,2-dimethyl-isothiourea hydriodic (23.2 g, 0.1 mol) followed by anhydrous sodium carbonate (11.7 g, 0.11 mol) and the mixture was heated to reflux for 3 hours. After cooling down, the precipitate was collected by filtration, washed with water to afford 6-bromo-2-methylamino-1H-quinazolin-4-one (16.5 g, 65 mmol, 65%) as a light yellow powder. 1H NMR (DMSO-d6): δ 11.20 (b, 1H), 7.91-7.90 (d, 1H), 7.64-7.63 (d, 1H), 7.20-7.18 (d, 1H), 6.30 (b, 1H), 2.82-2.81 (d, 3H).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 3 hours
  3. temperatureAfter cooling down
  4. filtrationthe precipitate was collected by filtration
  5. washwashed with water

Sources & evidence

ORD record
ord-bb105baebc4d4924b7b9b2c6c3bd8a2b
Source dataset
uspto-grants-2009_03
Patent number
US07501428B2

Reaction notes

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