Sodium Hydroxide → 2-[4-(4-Chlorobenzoyl)benzyl]thio-3-methyl-4(3H)-quinazolinone

HRID 1291241Notes

Reaction equation

HRID 1291241 reaction equation
[SH:1][C:2]1[N:11]([CH3:12])[C:10](=[O:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[OH-].[Na+].[Cl:16][C:17]1[CH:32]=[CH:31][C:20]([C:21]([C:23]2[CH:30]=[CH:29][C:26]([CH2:27]Br)=[CH:25][CH:24]=2)=[O:22])=[CH:19][CH:18]=1>C(O)C.CN(C=O)C.O>[Cl:16][C:17]1[CH:18]=[CH:19][C:20]([C:21]([C:23]2[CH:30]=[CH:29][C:26]([CH2:27][S:1][C:2]3[N:11]([CH3:12])[C:10](=[O:13])[C:9]4[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=4)[N:3]=3)=[CH:25][CH:24]=2)=[O:22])=[CH:31][CH:32]=1

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 98396514-(4-Chlorobenzoyl)benzyl bromideHCID 178481666HCID 178481666, compound

Product 1

HCID 189191702-[4-(4-Chlorobenzoyl)benzyl]thio-3-methyl-4(3H)-quinazolinoneYield 58.9%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2-Mercapto-3-methyl-4(3H)-quinazolinone (1.0 g) as synthesized by the method described in Chemical Pharmaceutical Bulletin 17, 2357, 1969 and sodium hydroxide (250 mg) were dissolved in 50% ethanol (15 ml)-DMF (15 ml). To this solution was added 4-(4-chlorobenzoyl)benzyl bromide (1.8 g) and the mixtrue was stirred at room temperature for 1 hour. This-reaction mixture was poured in water and the resulting crystals were collected by filtration, rinsed with water and methanol, and recrystallized from ethyl acetate-methanol to provide the title compound as colorless solid (1.29 g). 1H-NMR (CDCl3) δ: 3.61(3H,s), 4.62(2H,s), 7.35-7.50(3H,m), 7.55-7.80(8H,m), 8.24(1H,d,J=8.OHz).

Workup

  1. customThis-reaction mixture
  2. filtrationthe resulting crystals were collected by filtration
  3. washrinsed with water and methanol
  4. customrecrystallized from ethyl acetate-methanol

Sources & evidence

ORD record
ord-64266ba106d04c6997ca0b160668693a
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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