Triethyl orthoacetate → 4(3H)-Quinazolinone, 2-methyl-3-phenyl-

HRID 1367646Notes

Reaction equation

HRID 1367646 reaction equation
[NH2:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:5].[CH2:17](OC(OCC)(OCC)C)[CH3:18]>O>[CH3:17][C:18]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:4](=[O:5])[C:3]2[C:2](=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:1]=1

Participants

4

Reactant 2

HCID 66221Triethyl orthoacetateHCID 781422-Amino-N-phenylbenzamide

Product 1

HCID 633784(3H)-Quinazolinone, 2-methyl-3-phenyl-Yield 82%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-amino-N-phenyl-benzamide 26 (2 g, 0.009 mol) and 1,1,1-triethoxy-ethane (5.2 mL, 0.028 mol) were heated for 5 hours. The reaction mixture was poured into water, filtered off, washed with water yielding 2-methyl-3-phenyl-3H-quinazolin-4-one 27 (1.6 g, 82%). After recrystallization it was used in next step without further purification.

Workup

  1. temperaturewere heated for 5 hours
  2. filtrationfiltered off
  3. washwashed with water

Sources & evidence

ORD record
ord-df59e4b86edf4f8192becf472cc52b5f
Source dataset
uspto-grants-2011_02
Patent number
US07893260B2

Reaction notes

Loading…