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

HRID 592892Notes

Reaction equation

HRID 592892 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-aa88fa47c0354dc4bcd0aa5ddb04b6c7
Source dataset
uspto-grants-2016_01
Patent number
US09238655B2

Reaction notes

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