3-Chlorobenzaldehyde → HCID 59519059, compound

HRID 1161853Notes

Reaction equation

HRID 1161853 reaction equation
[NH2:1][C:2]1[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][C:3]=1[C:4]([NH:6][CH2:7][C:8](=[O:14])[NH:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:5].[Cl:20][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[CH:24]=O>C(O)(=O)C.C(O)C>[Br:19][C:16]1[CH:15]=[C:3]2[C:2](=[CH:18][CH:17]=1)[NH:1][CH:24]([C:23]1[CH:26]=[CH:27][CH:28]=[C:21]([Cl:20])[CH:22]=1)[N:6]([CH2:7][C:8]([NH:9][C:10]([CH3:12])([CH3:13])[CH3:11])=[O:14])[C:4]2=[O:5]

Participants

5

Reactant 2

HCID 114773-ChlorobenzaldehydeHCID 59519042HCID 59519042, compound

Product 1

HCID 59519059HCID 59519059, compoundYield 60.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

In a capped 20 mL scintillation vial, a solution of 2-amino-5-bromo-N-(tert-butylcarbamoylmethyl)benzamide (0.65 g, 2.0 mmol), 3-chlorobenzaldehyde (0.27 mL, 2.4 mmol) and catalytic glacial acetic acid (2 drops) in anhydrous ethanol (10 mL) was heated with stirring at 85° C. for 16 h. The resulting white suspension was cooled to room temperature, the white solid collected by suction filtration and washed with cold EtOH to give 2-[6-bromo-2-(3-chlorophenyl)-4-oxo-1,4-dihydro-2H-quinazolin-3-yl]-N-tert-butylacetamide (0.53 g, 1.21 mmol, 58%).

Workup

  1. temperatureThe resulting white suspension was cooled to room temperature
  2. filtrationthe white solid collected by suction filtration
  3. washwashed with cold EtOH

Sources & evidence

ORD record
ord-963c8e6b024f478f8a3151b00e7ca632
Source dataset
uspto-grants-2010_10
Patent number
US07820649B2

Reaction notes

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