Ethanol → 2-(2-ethoxyphenyl)-4-(3H)-quinazolone

HRID 1034404Notes

Reaction equation

HRID 1034404 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4](S(O)(=O)=O)=[CH:3][CH:2]=1.[NH:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][NH:14]C1=O.ClC1C(=O)C(C#N)=[C:27](C#N)[C:28](=[O:31])C=1Cl.C([OH:39])C>>[CH2:28]([O:31][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[C:11]1[NH:14][C:15](=[O:39])[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:12]=1)[CH3:27]

Participants

5

Reactant 4

HCID 702EthanolHCID 6101p-Toluenesulfonic acidHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 123607561,2,3,4-Tetrahydroquinazolin-2-one

Product 1

HCID 1360065732-(2-ethoxyphenyl)-4-(3H)-quinazolone

Procedure

An equimolar mixture of anthranilamide (136 mg, 1.0 mmole) and 2-ethoxybenzaldehyde (166 mg, 1.0 mmole) is suspended in methanol (30 mL) and heated to reflux for 3 hours. After cooling, the Schiff's base is isolated by vacuum filtration, suspended in ethanol (50 mL) containing p-toluenesulfonic acid (33 mg, 0.17 mmole), and heated to reflux for 1 hour. The resulting dihydroquinazolone is treated with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ, 227 mg, 1.0 mmole) and heating is continued as above for 1 hour. After cooling to room temperature, the precipitated solid is filtered and washed with methanol. The product is recrystallized from methanol to yield a colorless solid. 1H-NMR (CDCl3) δ:8.54 (d,1H);8.30 (d,1H); 7.77 (m,2H); 7.51-7.43 (m,2H); 7.15 (t,1H); 7.05 (d,1H); 4.30 (q,2H,-CH 2CH3); 1.60 (t,3H,-CH2CH3).

Workup

  1. temperatureheated
  2. temperatureto reflux for 1 hour
  3. temperatureheating
  4. customis continued as above for 1 hour
  5. filtrationthe precipitated solid is filtered
  6. washwashed with methanol
  7. customThe product is recrystallized from methanol
  8. customto yield a colorless solid

Sources & evidence

ORD record
ord-6f317d77ff7b418fb9af83da6e5baee9
Source dataset
uspto-grants-1994_05
Patent number
US05316906

Reaction notes

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