Methyl iodide → 141807-86-5

HRID 1292422Notes

Reaction equation

HRID 1292422 reaction equation
[CH2:1]([N:4]1[C:13](=[O:14])[C:12]2[NH:11][C:10](/[CH:15]=[CH:16]/[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[N:9][C:8]=2[N:7]([CH2:23][CH2:24][CH3:25])[C:5]1=[O:6])[CH2:2][CH3:3].[C:26](=O)([O-])[O-].[K+].[K+].CI>CN(C)C=O>[CH2:1]([N:4]1[C:13](=[O:14])[C:12]2[N:11]([CH3:26])[C:10](/[CH:15]=[CH:16]/[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)=[N:9][C:8]=2[N:7]([CH2:23][CH2:24][CH3:25])[C:5]1=[O:6])[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 10065736HCID 10065736, compound

Product 1

HCID 6448583141807-86-5Yield 84.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Compound 1 obtained in Example 1 (2.00 g, 5.90 mmol) was dissolved in 65 ml of N,N-dimethylformamide. To the solution were added 2.04 g (14.8 mmol) of potassium carbonate and then 0.74 ml (11.8 mmol) of methyl iodide, and the mixture was stirred at 50° C. for 30 minutes. After cooling, insoluble substances were removed by filtration, and 500 ml of water was added to the filtrate. The mixture was extracted three times with chloroform, and the combined organic layers were washed twice with water and twice with a saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent: 20% ethyl acetate/hexane), followed by recrystallization from ethanol/water to give 1.75 g (yield: 84%) of Compound 2 as white needles.

Workup

  1. temperatureAfter cooling
  2. custominsoluble substances were removed by filtration, and 500 ml of water
  3. additionwas added to the filtrate
  4. extractionThe mixture was extracted three times with chloroform
  5. washthe combined organic layers were washed twice with water and twice with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (eluent: 20% ethyl acetate/hexane)
  9. customfollowed by recrystallization from ethanol/water

Sources & evidence

ORD record
ord-d9c2c769df3343c8ab8d8e28ab0223ba
Source dataset
uspto-grants-1998_05
Patent number
US05756735

Reaction notes

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