Water → 4(3H)-Quinazolinone, 3-ethyl-2-((2-pyridinylmethyl)thio)-

HRID 1762428Notes

Reaction equation

HRID 1762428 reaction equation
C[O-].[Na+].Cl.Cl[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1.[CH2:13]([N:15]1[C:24](=[O:25])[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:17]=[C:16]1[SH:26])[CH3:14].O>CO>[CH2:13]([N:15]1[C:24](=[O:25])[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:17]=[C:16]1[S:26][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1)[CH3:14]

Participants

6

Reactant 4

HCID 962WaterHCID 23392Picolyl chloride hydrochlorideHCID 10942334Sodium MethoxideHCID 178462980HCID 178462980, compound

Product 1

HCID 30881964(3H)-Quinazolinone, 3-ethyl-2-((2-pyridinylmethyl)thio)-Yield 48.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

7.0 ml of 28% methanolic solution of sodium methoxide and 2.82 g of 2-chloromethylpyridine hydrochloride were added, in turn, to a solution of 3.56 g of 3-ethyl-2mercapto-4(3H)-quinazolinone in 50 ml of methanol, and the stirring was continued at room temperature for 4 hours. The reaction solution was poured into about 300 ml of water and extracted with chloroform. The extract was dried over sodium sulfate and the solvent was distilled off under reduced pressure. The residue was recrystallized from a mixture of ethyl acetate and diisopropyl ether, to give 2.47 g of the title compound.

Workup

  1. extractionextracted with chloroform
  2. dry with materialThe extract was dried over sodium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe residue was recrystallized from a mixture of ethyl acetate and diisopropyl ether

Sources & evidence

ORD record
ord-a7263763ed4e4783afac70d38e9fb497
Source dataset
uspto-grants-1989_05
Patent number
US04833144

Reaction notes

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