Hydrochloric Acid → HCID 3335159, compound

HRID 1828750Notes

Reaction equation

HRID 1828750 reaction equation
[CH2:1]([C:4]1O[C:8](=[O:10])[C:7]2[CH:11]=[CH:12][CH:13]=[CH:14][C:6]=2[N:5]=1)[CH2:2][CH3:3].[CH2:15]([NH2:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[OH-].[Na+].Cl>C(Cl)(Cl)Cl.C(O)CO.O>[CH2:15]([N:22]1[C:8](=[O:10])[C:7]2[C:6](=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:5]=[C:4]1[CH2:1][CH2:2][CH3:3])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 7504BenzylamineHCID 14798Sodium HydroxideHCID 823661HCID 823661, compound

Product 1

HCID 3335159HCID 3335159, compound

Reagents, catalysts & solvents 3

HCID 174Ethylene GlycolSolventHCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

A solution of 2-propyl-4H-3,1-benzoxazin-4-one (1—1, 2.84 g, 15.0 mmol, 1 equiv.) and benzylamine(1.77 g, 16.5 mmol, 1.10 equiv.) in chloroform (10 mL) was heated at reflux for 4 hours. The reaction mixture was concentrated and the residue was heated in a mixture of NaOH (60 mg, 1.5 mmol, 0.1 equiv.) in ethylene glycol (10 mL) at 135° C. for 5 hours. The reaction mixture was cooled and diluted with water. The pH of the resulting mixture was adjusted to 7 by the addition of 6 N HCl. The insoluble solid was collected by filtration and recrystallized from acetone/water to give 3-benzyl-2-propylquinazolin-4(3H)-one (1–2) as cream-colored crystals. 1H NMR (500 MHz,CDCl3)δ8.31 (d, J=8 Hz, 1H), 7.74 (t, J=7 Hz, 1H),7.66 (d,J=8 Hz, 1H), 7.46 (t, J=8 Hz, 1H), 7.32 (m, 2H), 7.26 (m, 1H), 7.18 (d, J=7 Hz, 2H), 2.72 (t, J=7 Hz, 2H), 1.80 (m, 2H), 0.99 (t, J=7 Hz, 3H).

Workup

  1. temperatureat reflux for 4 hours
  2. concentrationThe reaction mixture was concentrated
  3. temperatureThe reaction mixture was cooled
  4. filtrationThe insoluble solid was collected by filtration
  5. customrecrystallized from acetone/water

Sources & evidence

ORD record
ord-525ed0e297bf474aac7d5b0b297b799e
Source dataset
uspto-grants-2006_06
Patent number
US07060705B2

Reaction notes

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