Benzaldehyde → 1,2-Dihydro-2-phenyl-4-quinazolinamine hydrochloride

HRID 1418380Notes

Reaction equation

HRID 1418380 reaction equation
[ClH:1].Cl.[NH2:3][C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([NH2:8])=[NH:7].[CH:13](=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(O)C>[ClH:1].[C:14]1([CH:13]2[N:7]=[C:6]([NH2:8])[C:5]3[C:4](=[CH:12][CH:11]=[CH:10][CH:9]=3)[NH:3]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 240BenzaldehydeHCID 669893132-Aminobenzamidine dihydrochloride

Product 1

HCID 675688751,2-Dihydro-2-phenyl-4-quinazolinamine hydrochlorideYield 52.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-aminobenzamidine dihydrochloride (Example A) (1.0 g, 4.8 mmol) and benzaldehyde (0.48 ml, 5.8 mmol) in ethanol (30 ml) was heated at reflux for 2 hours. The solution was cooled and the solvent evaporated to give an oil which was purified by flash chromatography on aluminium oxide (Brockman 1, activated neutral) using dichloromethane/methanol as eluant to give a solid which was recrystallised from isopropyl alcohol to afford the title compound as a solid (0.65 g), m.p. 212°-214° C.

Workup

  1. temperatureat reflux for 2 hours
  2. temperatureThe solution was cooled
  3. customthe solvent evaporated
  4. customto give an oil which
  5. customwas purified by flash chromatography on aluminium oxide (Brockman 1, activated neutral)
  6. customto give a solid which
  7. customwas recrystallised from isopropyl alcohol

Sources & evidence

ORD record
ord-88131c1f34be4cea88f5fca832090124
Source dataset
uspto-grants-1999_03
Patent number
US05883102

Reaction notes

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