Methyl iodide → 5-(4-Chlorobenzyl)-2-methylthiopyrimid-4-one

HRID 614675Notes

Reaction equation

HRID 614675 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][C:7]2[C:8](=[O:14])[NH:9][C:10](=[S:13])[NH:11][CH:12]=2)=[CH:4][CH:3]=1.[CH3:17]I.[OH-].[Na+]>O.C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C:7]2[C:8](=[O:14])[NH:9][C:10]([S:13][CH3:17])=[N:11][CH:12]=2)=[CH:15][CH:16]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 43709225-(4-chlorobenzyl)-2-thiouracil

Product 1

HCID 129459805-(4-Chlorobenzyl)-2-methylthiopyrimid-4-oneYield 91.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 5-(4-chlorobenzyl)-2-thiouracil (50.5 g), methyl iodide (28.4 g) and sodium hydroxide (8.2 g) in water (200 ml) and ethanol (400 ml) was stirred at 60° for 30 minutes then allowed to cool. The crystalline product was filtered and washed with water to give 5-(4-chlorobenzyl)-2-methylthio-4-pyrimidone (48.6 g), m.p. 193°-194° (methanol/ethanol).

Workup

  1. temperatureto cool
  2. filtrationThe crystalline product was filtered
  3. washwashed with water

Sources & evidence

ORD record
ord-8e4e843f539c4515a339e998d776d251
Source dataset
uspto-grants-1979_03
Patent number
US04145546

Reaction notes

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