Acetic Acid → 4(1h)-Quinazolinone,2-[4-(2-chloroethoxy)phenyl]-2,3-dihydro-8-methoxy-3-(4-methoxyphenyl)-

HRID 617129Notes

Reaction equation

HRID 617129 reaction equation
[NH2:1][C:2]1[C:18]([O:19][CH3:20])=[CH:17][CH:16]=[CH:15][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1)=[O:5].[Cl:21][CH2:22][CH2:23][O:24][C:25]1[CH:32]=[CH:31][C:28]([CH:29]=O)=[CH:27][CH:26]=1.C(O)(=O)C>C(O)C>[Cl:21][CH2:22][CH2:23][O:24][C:25]1[CH:32]=[CH:31][C:28]([CH:29]2[N:6]([C:7]3[CH:8]=[CH:9][C:10]([O:13][CH3:14])=[CH:11][CH:12]=3)[C:4](=[O:5])[C:3]3[C:2](=[C:18]([O:19][CH3:20])[CH:17]=[CH:16][CH:15]=3)[NH:1]2)=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 1431564-(2-Chloroethoxy)benzaldehydeHCID 181744302-amino-N-(4-methoxy-phenyl)-3-methoxy-benzamide

Product 1

HCID 218510814(1h)-Quinazolinone,2-[4-(2-chloroethoxy)phenyl]-2,3-dihydro-8-methoxy-3-(4-methoxyphenyl)-Yield 80.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 20.05 g (0.0736 mol) of 2-amino-N-(4-methoxy-phenyl)-3-methoxy-benzamide in 400 mL of ethanol was added 13.6 g (0.0736 mol) of p-(2-chloro-ethoxy)-benzaldehyde (Frinton Labs), and 10 mL of acetic acid. The reaction mixture was stirred and heated to a mild reflux overnight. After cooling to room temperature, the solvent was evaporated in a rotary evaporator. The residue was dissolved in 300 mL of ethyl acetate and washed with water (4×100 mL). The organic phase was removed, dried over magnesium sulfate, filtered and evaporated to dryness in a rotary evaporator. The residual oil was placed under the vacuum pump, which yielded 26.0 g (mp 122-124° C.) of product.

Workup

  1. temperatureheated to
  2. temperaturea mild reflux overnight
  3. customthe solvent was evaporated in a rotary evaporator
  4. dissolutionThe residue was dissolved in 300 mL of ethyl acetate
  5. washwashed with water (4×100 mL)
  6. customThe organic phase was removed
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated to dryness in a rotary evaporator

Sources & evidence

ORD record
ord-3dd3a0e6e1824b0d834e0baa14bb7ca3
Source dataset
uspto-grants-1999_09
Patent number
US05948775

Reaction notes

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