2-(2-Ethoxybenzamido)-3-methylbenzamide → 2-(2-Ethoxyphenyl)-8-methylquinazolin-4(3H)-one
Reaction equation
[CH2:1]([O:3][C:4]1[CH:22]=[CH:21][CH:20]=[CH:19][C:5]=1[C:6]([NH:8][C:9]1[C:17]([CH3:18])=[CH:16][CH:15]=[CH:14][C:10]=1[C:11]([NH2:13])=[O:12])=O)[CH3:2]>ClCCl.CO.[Cl-].[Zn+2].[Cl-]>[CH2:1]([O:3][C:4]1[CH:22]=[CH:21][CH:20]=[CH:19][C:5]=1[C:6]1[NH:13][C:11](=[O:12])[C:10]2[C:9](=[C:17]([CH3:18])[CH:16]=[CH:15][CH:14]=2)[N:8]=1)[CH3:2]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 210 °C
Procedure
A mixture of 2-(2-ethoxybenzamido)-3-methylbenzamide (1.6 g, 0.0053 mol) and anhydrous zinc chloride (2.29 g, 0.016 mol) was heated at 210° C. for 5 minutes, then allowed to cool. The residue was dissolved in dichloromethane-methanol (90:10, 200 ml) and this solution washed with an aqueous solution of ethylenediamine tetraacetic acid disodium salt (12 g in 400 ml of water). The aqueous phase was then extracted with a mixture of dichloromethane-methanol (90:10, 2×50 ml) and the organic solutions combined, dried (Na2SO4) and evaporated under vacuum. The residue crystallized from ethanol to give the title compound as colourless needles (0.6 g, 40%), m.p. 177-180° C.
Workup
- temperatureto cool
- washthis solution washed with an aqueous solution of ethylenediamine tetraacetic acid disodium salt (12 g in 400 ml of water)
- extractionThe aqueous phase was then extracted with a mixture of dichloromethane-methanol (90:10, 2×50 ml)
- dry with materialdried (Na2SO4)
- customevaporated under vacuum
- customThe residue crystallized from ethanol
Sources & evidence
- ORD record
- ord-45c6c35f824a4e93a301b19385c47c07
- Source dataset
- uspto-grants-2003_05
- Patent number
- US06562830B1
Reaction notes
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