Methyl iodide → HCID 15586989, compound

HRID 544525Notes

Reaction equation

HRID 544525 reaction equation
[CH3:1][N:2]([CH3:18])[C:3]1[NH:4][N:5]=[C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][CH3:17])[C:7](=[O:9])[N:8]=1.[C:19](=O)=O.CC(C)=O.C([Li])CCC.CI>O1CCCC1.CCCCCC.CO>[CH3:19][N:4]1[C:3]([N:2]([CH3:18])[CH3:1])=[N:8][C:7](=[O:9])[C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][CH3:17])=[N:5]1

Participants

8

Reactant 4

HCID 6328Methyl iodideHCID 18522661Acetone cardiceHCID 178418339ButyllithiumHCID 178489421HCID 178489421, compound

Product 1

HCID 15586989HCID 15586989, compoundYield 90%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

3-Dimethylamino-6-(o-methoxyphenyl)-5-oxo-2,5-dihydro-1,2,4-triazine (0.5 g) was dissolved in tetrahydrofuran (40 ml), and the mixture was cooled to -30° C. with dry ice/acetone. A solution of n-butyl lithium in n-hexane (15%, 1.2 ml) was dropwise added to the mixture, which was then warmed to room temperature. To the resultant mixture, methyl iodide (0.42 g) was dropwise added and, upon completion of the addition, the resulting mixture was stirred at room temperature for 10 hours to complete the reaction. Then, methanol (10 ml) was added thereto, and the resultant mixture was evaporated to dryness under reduced pressure to give a crude product. Recrystallization of the crude product from ethanol gave 0.47 g of 2-methyl-3-dimethylamino-6-(o-methoxyphenyl)-5-oxo-2,5-dihydro-1,2,4-triazine in 90% yield. M.P., 202° C.

Workup

  1. customthe reaction
  2. customthe resultant mixture was evaporated to dryness under reduced pressure
  3. customto give a crude product
  4. customRecrystallization of the crude product from ethanol

Sources & evidence

ORD record
ord-295a926d0dea4447ab654571ab470be7
Source dataset
uspto-grants-1984_05
Patent number
US04451283

Reaction notes

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