Methyl iodide → 141807-96-7

HRID 1077447Notes

Reaction equation

HRID 1077447 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:25]=[CH:26][C:27]=1[O:28][CH3:29])/[CH:6]=[CH:7]/[C:8]1[NH:16][C:15]2[C:14](=[O:17])[N:13]([CH2:18][CH2:19][CH3:20])[C:12](=[O:21])[N:11]([CH2:22][CH2:23][CH3:24])[C:10]=2[N:9]=1.[C:30](=O)([O-])[O-].[K+].[K+].CI>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:25]=[CH:26][C:27]=1[O:28][CH3:29])/[CH:6]=[CH:7]/[C:8]1[N:16]([CH3:30])[C:15]2[C:14](=[O:17])[N:13]([CH2:18][CH2:19][CH3:20])[C:12](=[O:21])[N:11]([CH2:22][CH2:23][CH3:24])[C:10]=2[N:9]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 10475986HCID 10475986, compound

Product 1

HCID 6448585141807-96-7Yield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Compound B (1.20 g, 3.02 mmol) was dissolved in 20 ml of dimethylformamide. To the solution were added 1.04 g (7.55 mmol) of potassium carbonate and subsequently 0.38 ml (6.04 mmol) of methyl iodide, and the resultant mixture was stirred at 50° C. for 30 minutes. After cooling, insoluble matters were filtered off, and 400 ml of water was added to the filtrate. The mixture was extracted three times with 100 ml of chloroform. The extract was washed twice with water and once with a saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate, followed by evaporation under reduced pressure. The residue was purified by silica gel column chromatography (eluent: 1% methanol/chloroform), followed by recrystallization from propanol/water to give 1.22. g (yield 98%) of Compound 1 as white needles.

Workup

  1. temperatureAfter cooling
  2. filtrationinsoluble matters were filtered off
  3. addition400 ml of water was added to the filtrate
  4. extractionThe mixture was extracted three times with 100 ml of chloroform
  5. washThe extract was washed twice with water and once with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. customfollowed by evaporation under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (eluent: 1% methanol/chloroform)
  9. customfollowed by recrystallization from propanol/water
  10. customto give 1.22

Sources & evidence

ORD record
ord-76a340c5a42a4103883e3203b6e2778f
Source dataset
uspto-grants-1996_08
Patent number
US05543415

Reaction notes

Loading…