Water → 2-(4-Methylphenyl)quinazolin-4(3H)-one

HRID 1388236Notes

Reaction equation

HRID 1388236 reaction equation
[C:1]([C:4]1[CH:19]=[CH:18][CH:17]=[CH:16][C:5]=1[NH:6][C:7]([C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1)=O)(=[O:3])[NH2:2].[OH-].[Na+].O>C(O)(=O)C>[CH3:15][C:12]1[CH:13]=[CH:14][C:9]([C:7]2[NH:2][C:1](=[O:3])[C:4]3[C:5](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:6]=2)=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 8196472-[(4-methylbenzoyl)amino]benzamide

Product 1

HCID 1354521092-(4-Methylphenyl)quinazolin-4(3H)-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 2'-carbamoyl-p-toluanilide (66.97 g; 0.263 mol), sodium hydroxide (41.9 g) and water 837 ml) is stirred and heated at reflux for 0.5 hour. The resultant solution is cooled down, made acid with acetic acid. The reaction mixture is filtered, the isolated product is washed and dried to afford 58.16 g off white solid, mp 239°-241° C. Recrystallized from absolute ethanol, the product has a mp of 239°-240.5° C.

Workup

  1. temperatureheated
  2. temperatureat reflux for 0.5 hour
  3. filtrationThe reaction mixture is filtered
  4. washthe isolated product is washed
  5. customdried
  6. customto afford 58.16 g off white solid, mp 239°-241° C
  7. customRecrystallized from absolute ethanol

Sources & evidence

ORD record
ord-f041c9964c7241bf930d40ac3ff617ab
Source dataset
uspto-grants-1984_02
Patent number
US04431440

Reaction notes

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