Benzylamine → HCID 11724820, compound

HRID 973567Notes

Reaction equation

HRID 973567 reaction equation
Cl[C:2]1[N:11]=[C:10]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH3:19])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH2:20]([NH2:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(O)CCC>[CH2:20]([NH:27][C:2]1[N:11]=[C:10]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH3:19])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 10400899HCID 10400899, compound

Product 1

HCID 11724820HCID 11724820, compoundYield 55.2%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

2-Chloro-4-(2-methylphenylamino)quinazoline (2.7 g, 0.01 mol) and benzylamine (2.4 g, 0.022 mol) were dissolved in n-butanol (20 ml) and heated under reflux for 5 hours. The solution was cooled, excess solvent removed in vacuo and the residue treated with water, filtered and crystallised from ethanol/water. The compound was then chromatographed (silica gel, 0.5% methanolic ammonia/chloroform) to afford an oil, which on trituration with ether gave crystals of 2-benzylamino-4-(2-methylphenylamino)quinazoline (1.88 g, 55%), m.p. 127°-130°.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 5 hours
  3. temperatureThe solution was cooled
  4. customexcess solvent removed in vacuo
  5. additionthe residue treated with water
  6. filtrationfiltered
  7. customcrystallised from ethanol/water
  8. customThe compound was then chromatographed (silica gel, 0.5% methanolic ammonia/chloroform)
  9. customto afford an oil, which on trituration with ether

Sources & evidence

ORD record
ord-6a985687a5824547b5c6292610189019
Source dataset
uspto-grants-1991_11
Patent number
US05064833

Reaction notes

Loading…