Benzaldehyde → 2-Phenyl-4(3H)-Quinazolinone

HRID 1017516Notes

Reaction equation

HRID 1017516 reaction equation
S([O-])(O)=O.[Na+].[NH2:6][C:7]1[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=1[C:9]([NH2:11])=[O:10].[CH:16](=O)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C)C(=O)C>[C:17]1([C:16]2[NH:11][C:9](=[O:10])[C:8]3[C:7](=[CH:15][CH:14]=[CH:13][CH:12]=3)[N:6]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 6942AnthranilamideHCID 23665763Sodium Bisulfite

Product 1

HCID 1354004562-Phenyl-4(3H)-Quinazolinone

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
150 °C

Procedure

Sodium hydrogen sulfite (0.8 g, 7.5 mmol) was added to a solution of 2-aminobenzamide (30) (1.0 g, 7.3 mmol) and benzaldehyde (32) (0.8 g, 7.3 mmol) in N,N-dimethylacetamide (DMAC) (20 ml). The mixture was heated with stirring at 150° C. for 2 h and then poured into ice water (200 ml). The precipitate was collected, washed with water, and then dried in vacuo. After recrystallization from EtOH, 41 was obtained (1.5 g, 92.6%) as pale yellow needles. Yield, mp, and spectral data are given in Table 1.

Workup

  1. temperatureThe mixture was heated
  2. customThe precipitate was collected
  3. washwashed with water
  4. customdried in vacuo
  5. customAfter recrystallization from EtOH
  6. custom41 was obtained (1.5 g, 92.6%) as pale yellow needles
  7. customYield

Sources & evidence

ORD record
ord-32c1ff83fd39480d9838c5f012b8ee5b
Source dataset
uspto-grants-2002_11
Patent number
US06479499B1

Reaction notes

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