Water → 3-Phenyl-2-[(4-methylpyridin-2-yl)methylthio]-4(3H)-quinazolinone

HRID 1762430

Reaction equation

HRID 1762430 reaction equation
C[O-].[Na+].[SH:4][C:5]1[N:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:13](=[O:21])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=1.Cl.Cl[CH2:24][C:25]1[CH:30]=[C:29]([CH3:31])[CH:28]=[CH:27][N:26]=1.O>CO>[C:15]1([N:14]2[C:13](=[O:21])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[N:6]=[C:5]2[S:4][CH2:24][C:25]2[CH:30]=[C:29]([CH3:31])[CH:28]=[CH:27][N:26]=2)[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10942334Sodium MethoxideHCID 200610712-(Chloromethyl)-4-methylpyridine hydrochlorideHCID 178515047HCID 178515047, compound

Product 1

HCID 145751693-Phenyl-2-[(4-methylpyridin-2-yl)methylthio]-4(3H)-quinazolinoneYield 30.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

8.7 ml of 28% methanolic solution of sodium methoxide were added to a solution of 5.0 g of 2-mercapto-3-phenyl-4(3H)-quinazolinone and 4.0 g of 2-chloromethyl-4-methylpyridine hydrochloride in methanol, and the stirring was continued at room temperature for 5 hours. The reaction solution was poured into water and extracted with chloroform. The chloroform layer was washed with an aqueous solution of sodium carbonate and dried over sodium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography. The fraction eluted with 8% ethyl acetate in chloroform was collected and crystallized from ethyl acetate to give 2.17 g (30.7%) of the title compound.

Workup

  1. extractionextracted with chloroform
  2. washThe chloroform layer was washed with an aqueous solution of sodium carbonate
  3. dry with materialdried over sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe residue was purified by silica gel column chromatography
  6. washThe fraction eluted with 8% ethyl acetate in chloroform
  7. customwas collected
  8. customcrystallized from ethyl acetate

Sources & evidence

ORD record
ord-fad592df122847eaa7aa81aff6bf3215
Source dataset
uspto-grants-1989_05
Patent number
US04833144

Linked notes

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