Methyl iodide → HCID 117830788, compound

HRID 515917Notes

Reaction equation

HRID 515917 reaction equation
[OH-].[K+].[Br:3][C:4]1[C:5]([CH3:21])=[C:6]([C:19]#[N:20])[N:7](S(C2C=CC(C)=CC=2)(=O)=O)[CH:8]=1.[H-].[Na+].I[CH3:25]>CO.O1CCCC1>[Br:3][C:4]1[C:5]([CH3:21])=[C:6]([C:19]#[N:20])[N:7]([CH3:25])[CH:8]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 24758Sodium hydrideHCID 117830942HCID 117830942, compound

Product 1

HCID 117830788HCID 117830788, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Potassium hydroxide (3.65 g, 65.1 mmol) is added all at once to a suspension of 4-bromo-3-methyl-1-(4-methylbenzenesulphonyl)-1H-pyrrole-2-carbonitrile (4.66 g, 13.7 mmol) in methanol (95 mL) cooled using an ice bath. After 15 minutes, the suspension is stirred at ambient temperature for 17 hours. The methanol is evaporated to dryness. The evaporation residue is taken up in MTBE (25 mL) and washed with water (25 mL). The aqueous phase is extracted with MTBE (2×25 mL). The combined organic phases are dried over Na2SO4, filtered and concentrated in vacuo. The residue obtained is dissolved in tetrahydrofuran (50 mL) and the solution is cooled using an ice bath. NaH (60% in oil) (1.02 g, 25.5 mmol) is added. After 10 minutes, iodomethane (2.4 mL, 38.6 mmol) is also added. The mixture is stirred at ambient temperature for 1.5 hours. The tetrahydrofuran is evaporated to dryness. The residue is taken up in dichloromethane and washed with water. The aqueous phase is extracted with dichloromethane. The combined organic phases are dried over Na2SO4, filtered and concentrated in vacuo to obtain the expected compound in the form of a solid.

Workup

  1. temperaturecooled
  2. customThe methanol is evaporated to dryness
  3. washwashed with water (25 mL)
  4. extractionThe aqueous phase is extracted with MTBE (2×25 mL)
  5. dry with materialThe combined organic phases are dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue obtained
  9. temperaturethe solution is cooled
  10. waitAfter 10 minutes
  11. stirringThe mixture is stirred at ambient temperature for 1.5 hours
  12. customThe tetrahydrofuran is evaporated to dryness
  13. washwashed with water
  14. extractionThe aqueous phase is extracted with dichloromethane
  15. dry with materialThe combined organic phases are dried over Na2SO4
  16. filtrationfiltered
  17. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-aed34ff96685447a8229c144a346a868
Source dataset
uspto-grants-2015_08
Patent number
US09108983B2

Reaction notes

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