Methyl iodide → HCID 53824101, compound

HRID 1647848Notes

Reaction equation

HRID 1647848 reaction equation
[O:1]1[CH2:5][CH2:4][CH:3]([CH2:6][N:7]2[CH2:12][N:11]([CH3:13])[CH2:10][NH:9][C:8]2=[N:14][N+:15]([O-:17])=[O:16])[CH2:2]1.[H-].[Na+].[CH3:20]I>CN(C=O)C>[O:1]1[CH2:5][CH2:4][CH:3]([CH2:6][N:7]2[CH2:12][N:11]([CH3:13])[CH2:10][N:9]([CH3:20])[C:8]2=[N:14][N+:15]([O-:17])=[O:16])[CH2:2]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 136401241HCID 136401241, compound

Product 1

HCID 53824101HCID 53824101, compoundYield 45.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture comprising 3.00 g of 1-{(tetrahydro-3-furanyl)methyl}-2-(nitroimino)-5-methylhexahydro-1,3,5-triazine, 0.54 g of sodium hydride and 40 ml of DMF was stirred at 50° C. for 30 minutes. Then, 2.08 g of methyl iodide were added thereto, followed by stirring at 70° C. for 2 hours. The reaction fluid was poured into a saturated saline solution and the mixture was extracted with methylene chloride several times. The methylene chloride solution was dried over anhydrous sodium sulfate and concentrated under a reduced pressure. The crude oily matter thus obtained was purified by column chromatography to obtain 1.43 g of 1-{(tetrahydro-3-furanyl)methyl}-2-(nitroimino)-3,5-dimethylhexahydro-1,3,5-triazine.

Workup

  1. stirringby stirring at 70° C. for 2 hours
  2. additionThe reaction fluid was poured into a saturated saline solution
  3. extractionthe mixture was extracted with methylene chloride several times
  4. dry with materialThe methylene chloride solution was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under a reduced pressure
  6. customThe crude oily matter thus obtained
  7. customwas purified by column chromatography

Sources & evidence

ORD record
ord-6deb10c0214b41288a2cda6396f46a10
Source dataset
uspto-grants-1995_07
Patent number
US05434181

Reaction notes

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