Dimethylformamide → 2-[4-(2,4-Dichlorobenzoyl)benzyl]thio-3-methyl-4(3H)-quinazolinone

HRID 1291244Notes

Reaction equation

HRID 1291244 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+].CN(C=O)C.[Cl:21][C:22]1[CH:37]=[C:36]([Cl:38])[CH:35]=[CH:34][C:23]=1[C:24]([C:26]1[CH:33]=[CH:32][C:29]([CH2:30]Br)=[CH:28][CH:27]=1)=[O:25]>C(O)C.O>[Cl:21][C:22]1[CH:37]=[C:36]([Cl:38])[CH:35]=[CH:34][C:23]=1[C:24]([C:26]1[CH:27]=[CH:28][C:29]([CH2:30][S:1][C:2]2[N:11]([CH3:12])[C:10](=[O:13])[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[N:3]=2)=[CH:32][CH:33]=1)=[O:25]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 189192794-(2,4-Dichlorobenzoyl)benzyl bromideHCID 178481666HCID 178481666, compound

Product 1

HCID 189193372-[4-(2,4-Dichlorobenzoyl)benzyl]thio-3-methyl-4(3H)-quinazolinoneYield 91.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 2-mercapto-3-methyl-4(3H)-quinazolinone (1.0 g) and sodium hydroxide (250 mg) in 50% ethanol (15 ml)-DMF (15 ml) was added 4-(2,4-dichlorobenzoyl)benzyl bromide (1.88 g) and the mixture was stirred at room temperature for 1 hour. This reaction mixtrue was poured in water and the resulting crystals were collected by filtration, rinsed with water and methanol, and recrystallized from methanol to provide the title compound as colorless solid (2.16 g). IH-NMR (CDCl3) δ: 3.59(3H,s), 4.59(2H,s), 7.25-7.80(10H,m), 8.22(1H,dd,J=8.2,1.4Hz).

Workup

  1. filtrationthe resulting crystals were collected by filtration
  2. washrinsed with water and methanol
  3. customrecrystallized from methanol

Sources & evidence

ORD record
ord-970672ce441a42019c7b678f497f586b
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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