Acetanilide → 4(1H)-Quinazolinone

HRID 963605Notes

Reaction equation

HRID 963605 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)(=O)C.[C:11](=O)([O:13]CC)[NH2:12].O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>>[N:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:11](=[O:13])[NH:12][CH:1]=1

Participants

4

Reactant 3

HCID 904Acetanilide2×HCID 5641Carbamic acid, ethyl esterHCID 14812Phosphorus oxide (P4O10)

Product 1

HCID 1354087534(1H)-Quinazolinone

Procedure

From acetanilide. Acetanilide reacts with ethyl carbamate in the presence of phosphorous pentoxide to produce 4-quinazolone. For unsymmetrical 4-quinazolones this reaction produces a mixture of regioisomers, thereby complicating the isolation and lowering the yield. ##STR7##

Sources & evidence

ORD record
ord-7f07929e31c241a9b927b2db274803ee
Source dataset
uspto-grants-1998_06
Patent number
US05763608

Reaction notes

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