Sodium Carbonate → HCID 18796730, compound

HRID 1900657Notes

Reaction equation

HRID 1900657 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:15]=[C:14](Cl)[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([Cl:17])[CH:12]=2)[N:7]=1)=[O:5])[CH3:2].[CH2:18]([NH2:28])[C:19]1[CH:27]=[CH:26][C:25]2[O:24][CH2:23][O:22][C:21]=2[CH:20]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)(C)C>[CH2:1]([O:3][C:4]([C:6]1[N:15]=[C:14]([NH:28][CH2:18][C:19]2[CH:27]=[CH:26][C:25]3[O:24][CH2:23][O:22][C:21]=3[CH:20]=2)[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([Cl:17])[CH:12]=2)[N:7]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 75799Benzo-1,3-dioxole-5-methylamineHCID 18796671Ethyl 4,6-dichloroquinazoline-2-carboxylate

Product 1

HCID 18796730HCID 18796730, compoundYield 92.3%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

2.72 g (0.0100 mol) of 2-ethoxycarbonyl-4,6-dichloroquinazoline, 1.75 g (0.0116 mol) of piperonylamine and 1.60 g (0.0151 mol) of sodium carbonate were mixed with 100 ml of isopropyl alcohol. The obtained mixture was heated under reflux for 24 hours and distilled under a reduced pressure to remove the solvent. The residue was purified by silica gel column chromatography and recrystallized from chloroform/n-hexane to give 3.56 g of the title compound as a colorless needle.

Workup

  1. temperatureThe obtained mixture was heated
  2. temperatureunder reflux for 24 hours
  3. distillationdistilled under a reduced pressure
  4. customto remove the solvent
  5. customThe residue was purified by silica gel column chromatography
  6. customrecrystallized from chloroform/n-hexane

Sources & evidence

ORD record
ord-e77c6c51b7124eba81d03522ebb43f25
Source dataset
uspto-grants-1996_11
Patent number
US05576322

Reaction notes

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