Hydroxyamine hydrochloride → 1-Methyl-4-phenyl-6-chloro-2-quinazolinone

HRID 128034Notes

Reaction equation

HRID 128034 reaction equation
[C:1]([C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[N:16]([CH3:26])[C:17]([NH:19]C1C=CC=CC=1)=[O:18])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.NO>C(O)C>[Cl:15][C:13]1[CH:14]=[C:9]2[C:10](=[CH:11][CH:12]=1)[N:16]([CH3:26])[C:17](=[O:18])[N:19]=[C:1]2[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 234716281-(2-Benzoyl-4-chlorophenyl)-1-methyl-3-phenylurea

Product 1

HCID 631341-Methyl-4-phenyl-6-chloro-2-quinazolinoneYield 66.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3.65 g (0.01 mole) of 1-(2-benzoyl-4-chlorophenyl)-1-methyl-3-phenylurea and 2.09 g (0.03 mole) of hydroxylamine hydrochloride in 50 ml of ethanol was stirred and refluxed for 5 days. The reaction mixture was cooled, and the suspended solid was collected on a filter, washed with alcohol, and dried in air to give 1.80 g (63%) of 6-chloro-1-methyl-4-phenyl-2-(1H)-quinazolinone as yellow crystals, mp 289°-291°.

Workup

  1. temperaturerefluxed for 5 days
  2. temperatureThe reaction mixture was cooled
  3. customthe suspended solid was collected on a filter
  4. washwashed with alcohol
  5. customdried in air

Sources & evidence

ORD record
ord-4ea04c02e3644d9da28164a33930534b
Source dataset
uspto-grants-1981_03
Patent number
US04258187

Reaction notes

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