Dimethylformamide → 3-Bromo-5-iodo-1-methyl-1,2-dihydropyridin-2-one

HRID 1021961Notes

Reaction equation

HRID 1021961 reaction equation
[CH3:1][N:2]([CH:4]=[O:5])[CH3:3].[Br:6][C:7]1C(O)=NC=[C:11]([I:13])[CH:12]=1.IC.C([O-])([O-])=O.[K+].[K+]>O>[Br:6][C:7]1[C:4](=[O:5])[N:2]([CH3:3])[CH:1]=[C:11]([I:13])[CH:12]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178517796HCID 178517796, compound

Product 1

HCID 866840253-Bromo-5-iodo-1-methyl-1,2-dihydropyridin-2-oneYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer was charged with DMF (50 mL), 214a (6.0 g, 20.0 mmol), iodomethane (4.26 g, 30.0 mmol), and K2CO3 (5.52 g, 40.0 mmol). The mixture was stirred at room temperature for 2 h and diluted with water (200 mL). The resulting white solid was collected by filtration to afford 214b (5.97 g, 95%) as a white solid. MS-ESI: [M+H]+ 314

Workup

  1. customA 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer
  2. filtrationThe resulting white solid was collected by filtration

Sources & evidence

ORD record
ord-5188ea3c51a84b24a238c8f4aca285e9
Source dataset
uspto-grants-2014_05
Patent number
US08716274B2

Reaction notes

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