Picolyl chloride hydrochloride → 6-Methyl-3-phenyl-2-(2-pyridylmethylthio)-4(3H)-quinazolinone

HRID 1085062Notes

Reaction equation

HRID 1085062 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]=[C:10]([CH3:22])[CH:11]=2)[N:6]=1.Cl.Cl[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=1>CO>[CH3:22][C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][CH:9]=1)[N:6]=[C:5]([S:4][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=1)[N:14]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:13]2=[O:21]

Participants

5

Reactant 3

HCID 23392Picolyl chloride hydrochlorideHCID 10942334Sodium MethoxideHCID 178423443HCID 178423443, compound

Product 1

HCID 145751596-Methyl-3-phenyl-2-(2-pyridylmethylthio)-4(3H)-quinazolinoneYield 52.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

9.5 ml of 28% methanolic solution of sodium methoxide were added to a solution of 6.0 g of 2-mercapto-6-methyl-3- phenyl-4(3H)-quinazolinone and 4.0 g of 2-chloromethylpyridine hydrochloride in methanol, the mixture was stirred at room temperature for 2 hours and allowed to stand overnight. Crystals precipitated were collected by filtration and recrystallized from ethyl acetate to give 4.2 g (52.2%) of the title compound.

Workup

  1. waitto stand overnight
  2. customCrystals precipitated
  3. filtrationwere collected by filtration
  4. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-3e1669cc147d42d9ab1c69b7b1132683
Source dataset
uspto-grants-1991_04
Patent number
US05008266

Reaction notes

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