Sodium Acetate → HCID 18176138, compound

HRID 394767Notes

Reaction equation

HRID 394767 reaction equation
[C:1]([O-])(=[O:3])[CH3:2].[Na+].[Br:6][C:7]1[CH:8]=[C:9]([NH:13][C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([NH:24][C:25]([CH:27]=[CH:28][C:29](O)=[O:30])=[O:26])[CH:22]=3)[N:17]=[CH:16][N:15]=2)[CH:10]=[CH:11][CH:12]=1>C(OC(=O)C)(=O)C>[Br:6][C:7]1[CH:8]=[C:9]([N:13]([C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([N:24]4[C:29](=[O:30])[CH:28]=[CH:27][C:25]4=[O:26])[CH:22]=3)[N:17]=[CH:16][N:15]=2)[C:1](=[O:3])[CH3:2])[CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 53786874HCID 53786874, compound

Product 1

HCID 18176138HCID 18176138, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

Sodium acetate (0.10 g, 1.2 mmol) was added to a suspension of 3-[4-(3-bromo-phenylamino)-quinazolin-6-ylcarbamoyl]-acrylic acid (Z) (0.25 g, 0.61 mmol) in 5 mL of acetic anhydride, and the mixture was heated under reflux for 30 minutes. After cooling to room temperature, the reaction was filterd and the filtrate concentrated to dryness in vacuo. The residue was taken up in EtOAc and washed sequentially with saturated sodium bicarbonate, water, and brine. The EtOAc portion was dried over magnesium sulfate, filtered and concentrated to afford a faintly pink solid. The solid was recrystallized twice from EtOAc to afford N-(3-bromo-phenyl)-N-[6-(2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-quinazolin-4-yl]-acetamide (0.104 g, 39%) as an off-white powder, mp 174-175° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 30 minutes
  3. concentrationthe filtrate concentrated to dryness in vacuo
  4. washwashed sequentially with saturated sodium bicarbonate, water, and brine
  5. dry with materialThe EtOAc portion was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto afford a faintly pink solid
  9. customThe solid was recrystallized twice from EtOAc

Sources & evidence

ORD record
ord-4b2b81eb933e4db1a10989fffc8b4d28
Source dataset
uspto-grants-2003_08
Patent number
US06602863B1

Reaction notes

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