Sodium Hydroxide → HCID 18918904, compound

HRID 1291301Notes

Reaction equation

HRID 1291301 reaction equation
[CH3:1][N:2]1[C:11](=[O:12])[C:10]2[C:5](=[N:6][CH:7]=[CH:8][N:9]=2)[NH:4][C:3]1=[S:13].[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.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:13][C:3]3[N:2]([CH3:1])[C:11](=[O:12])[C:10]4[C:5](=[N:6][CH:7]=[CH:8][N:9]=4)[N:4]=3)=[CH:25][CH:24]=2)=[O:22])=[CH:31][CH:32]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 98396514-(4-Chlorobenzoyl)benzyl bromideHCID 15563341HCID 15563341, compound

Product 1

HCID 18918904HCID 18918904, compoundYield 28%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 3-methylpteridin-4-one-2-thione, (194 mg) in ethanol (5 ml) were added 1N-aqueous sodium hydroxide solution (1.2 ml) and 4-(4-chlorobenzoyl) benzyl bromide (310 mg) and the mixture was stirred at room temperature for 24 hours. The reaction mixture was diluted with water and extracted with ethyl acetate. The extract was washed with saturated aqueous NaCl solution and dried over anhydrous sodium sulfate. The solvent was then distilled off and the residue was purified by silica gel column chromatography (ethyl acetate) to provide the title compound as white powder (118 mg, 28%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with saturated aqueous NaCl solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was then distilled off
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-8271a5c92c32472383f5e29f9ee34131
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

Loading…