Methyl iodide → HCID 18315859, compound

HRID 275764Notes

Reaction equation

HRID 275764 reaction equation
[C:1]1([C:7]2[C:8](=[O:20])[NH:9][C:10]([Cl:19])=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[Br-].[Li+].[CH3:25]I>O.CN(C)C=O.COCCOC>[CH3:25][N:9]1[C:10]([Cl:19])=[C:11]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:12]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:8]1=[O:20]

Participants

8

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 82050Lithium BromideHCID 13123630HCID 13123630, compound

Product 1

HCID 18315859HCID 18315859, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a cooled (0° C.) solution of 3,5-diphenyl-6-chloro-1H-pyrazin-2-one (1.2 g; prepared by the method of Cheeseman et al, J. Chem. Soc. Chem. Comm. 1971, (18), 2977-2979) in 4:1 ethylene glycol dimethylether: dimethylformamide (25 cm3)was added sodium hydride (0.28 g). The reaction was stirred for 5 minutes at 0° C. under nitrogen whereupon lithium bromide (1.17 g) was added. After a further 5 minutes stirring at room temperature, under nitrogen, methyl iodide (4.78 g) was added. The mixture was stirred at room temperature overnight under nitrogen. The reaction was diluted with water and extracted with ethyl acetate. The organic phase was separated, dried over sodium sulphate and evaporated in vacuo. The residue was subjected to chromatography on silica gel using ethyl acetate as eluant to afford 1-methyl-3,5-diphenyl-6-chloro-1H-pyrazin-2-one as a yellow solid (1.2 g; 60%). Found C, 68.98; H, 4.31; N, 8.98% C17H13N2OCl requires C, 68.81; H, 4.42; N, 9.44%.m/e (ES+) 297/299 (M+H)+.

Workup

  1. customprepared by the method of Cheeseman et al, J
  2. additionwas added
  3. stirringThe mixture was stirred at room temperature overnight under nitrogen
  4. extractionextracted with ethyl acetate
  5. customThe organic phase was separated
  6. dry with materialdried over sodium sulphate
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-ad93bf413d4149cab82f9c0a9229c488
Source dataset
uspto-grants-2002_03
Patent number
US06352994B2

Reaction notes

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