4,6-Dichloroquinazoline → 4-(4-Chloro-3-nitrobenzyl)amino-6-chloroquinazoline

HRID 1003504Notes

Reaction equation

HRID 1003504 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([Cl:12])[CH:10]=2)[N:5]=[CH:4][N:3]=1.Cl.[Cl:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19][NH2:20])=[CH:17][C:16]=1[N+:23]([O-:25])=[O:24]>C(O)(C)C.C(N(CC)CC)C>[Cl:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19][NH:20][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([Cl:12])[CH:10]=3)[N:5]=[CH:4][N:3]=2)=[CH:17][C:16]=1[N+:23]([O-:25])=[O:24]

Participants

5

Reactant 2

HCID 2460244,6-DichloroquinazolineHCID 18796739(4-Chloro-3-nitrobenzyl)amine hydrochloride

Product 1

HCID 187967424-(4-Chloro-3-nitrobenzyl)amino-6-chloroquinazolineYield 92.6%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8471TriethylamineSolvent

Procedure

3.00 g (0.015 mol) of 4,6-dichloroquinazoline and 3.80 g (0.0170 mol) of 4-chloro-3-nitrobenzylamine hydrochloride were dissolved in a mixture comprising 100 ml of isopropyl alcohol and 15 ml of triethylamine. The obtained solution 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 (chloroform/ethyl acetate) and recrystallized from chloroform/n-hexane to give 4.85 g of the title compounds as a pale-yellow crystal.

Workup

  1. temperatureThe obtained solution 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 (chloroform/ethyl acetate)
  6. customrecrystallized from chloroform/n-hexane

Sources & evidence

ORD record
ord-7b20296534634a0fb0e54809962b9824
Source dataset
uspto-grants-2000_04
Patent number
US06046206

Reaction notes

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