Ethyl orthopropionate → 4(1H)-Quinazolinone

HRID 904645Notes

Reaction equation

HRID 904645 reaction equation
N[C:2]1[CH:15]=[CH:14][C:13](C)=[CH:12][C:3]=1[C:4]([NH:6][C:7]1NN=N[N:8]=1)=[O:5].C(OC(OCC)(OCC)CC)C>COCCO>[N:8]1[C:12]2[C:3](=[CH:2][CH:15]=[CH:14][CH:13]=2)[C:4](=[O:5])[NH:6][CH:7]=1

Participants

4

Reactant 2

HCID 66995Ethyl orthopropionateHCID 178426476HCID 178426476, compound

Product 1

HCID 1354087534(1H)-Quinazolinone

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

A slurry of 7.0 g of 2-amino-5-methyl-N-(1H-tetrazol-5-yl)benzamide and 5.7 g of 1,1,1-triethoxypropane in 50 ml of 2-methoxyethanol was heated at reflux for 48 hours. The solution was cooled and concentrated to a small volume. The resulting solid was then collected and air dried to give 2-ethyl-6-methyl-3-(1H)-tetrazol-5-yl)-4(3H)-quinazolinone melting at about 204°-205° C., after recrystallization from a mixture of dimethylformamide and water.

Workup

  1. temperatureat reflux for 48 hours
  2. temperatureThe solution was cooled
  3. concentrationconcentrated to a small volume
  4. customThe resulting solid was then collected
  5. customair dried

Sources & evidence

ORD record
ord-b44e4d1bcecb40d5a7144c0af8ee7fd1
Source dataset
uspto-grants-1983_12
Patent number
US04419357

Reaction notes

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