Water → HCID 136004603, compound

HRID 547458Notes

Reaction equation

HRID 547458 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:18])[NH:7][C:8]([CH2:12][C:13]([N:15]([CH3:17])[CH3:16])=[O:14])=[N:9]2)=[CH:4][CH:3]=1.C([O-])(=O)C.[Na+].[Br:24]Br.O>C(O)(=O)C>[Br:24][CH:12]([C:8]1[NH:7][C:6](=[O:18])[C:5]2[C:10](=[CH:11][C:2]([Cl:1])=[CH:3][CH:4]=2)[N:9]=1)[C:13]([N:15]([CH3:17])[CH3:16])=[O:14]

Participants

6

Reactant 4

HCID 962WaterHCID 24408BromineHCID 517045Sodium AcetateHCID 136004605HCID 136004605, compound

Product 1

HCID 136004603HCID 136004603, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a mixture of 2-(7-chloro-4-oxo-3,4-dihydroquinazolin-2-yl)-N,N-dimethylacetamide and sodium acetate (930 mg, 3 eq.) in acetic acid (15 ml), was added bromine (190 ul, 1 eq.). The reaction mixture was stirred at room temperature overnight. Water was added and the product was extracted into ethyl acetate. The ethyl acetate layer was washed several times with water, saturated sodium bicarbonate, saturated sodium chloride, dried over magnesium sulfate, filtered, and concentrated to give 2-bromo-2-(7-chloro-4-oxo-3,4-dihydroquinazolin-2-yl)-N,N-dimethylacetamide (0.95 g) as a brown solid.

Workup

  1. extractionthe product was extracted into ethyl acetate
  2. washThe ethyl acetate layer was washed several times with water, saturated sodium bicarbonate, saturated sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e6c18811eb95470fb23a0dbf51b49e1b
Source dataset
uspto-grants-2011_05
Patent number
US07939539B2

Reaction notes

Loading…