Methyl iodide → HCID 78128153, compound

HRID 1483166Notes

Reaction equation

HRID 1483166 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[O:12][C:11](=[O:13])[NH:10][CH2:9]2)=[N:6][CH:7]=1.[H-].[Na+].I[CH3:17]>O1CCCC1.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[O:12][C:11](=[O:13])[N:10]([CH3:17])[CH2:9]2)=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 78128152HCID 78128152, compound

Product 1

HCID 78128153HCID 78128153, compoundYield 85.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Compound 14b (350 mg, 1.44 mmol) was dissolved in dried tetrahydrofuran, cooled to 0° C. NaH (86.4 mg, 2.16 mmol) was added, and iodomethane (0.18 mL, 2.88 mmol) was added dropwise. After the addition was completed, the reaction mixture was raised to room temperature for reacting overnight. The reaction was monitored by TLC (petroleum ether/ethyl acetate=5/1). After the reaction completed, the mixture was diluted with water, and extracted with ethyl acetate. The organic phase was combined, washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate. Column chromatography (petroleum ether/ethyl acetate=8/1) afforded 315 mg of white solid (compound 14c), yield 85%.

Workup

  1. additionAfter the addition
  2. temperaturethe reaction mixture was raised to room temperature
  3. extractionextracted with ethyl acetate
  4. washwashed with saturated sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate

Sources & evidence

ORD record
ord-f2810e658be445d3a4e7ab3a5ffb9aa5
Source dataset
uspto-grants-2016_08
Patent number
US09416144B2

Reaction notes

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