Methyl iodide → HCID 9906070, compound

HRID 1590565Notes

Reaction equation

HRID 1590565 reaction equation
[CH3:1]C(C)([O-])C.[K+].[Br:7][C:8]1[NH:9][C:10]([Br:16])=[C:11]([Br:15])[C:12]=1[C:13]#[N:14].CI.CCCCCC>C1COCC1.O.C(OCC)(=O)C>[CH3:1][N:9]1[C:10]([Br:16])=[C:11]([Br:15])[C:12]([C:13]#[N:14])=[C:8]1[Br:7]

Participants

8

Reactant 4

HCID 6328Methyl iodideHCID 8058HexaneHCID 10471741HCID 10471741, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 9906070HCID 9906070, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred mixture of 0.87 g (7.75 mmol) of potassium t-butoxide in 30 mL of dry THF under a nitrogen atmosphere is added dropwise from an addition funnel 2.10 g (6.39 mmol) of 2,4,5-tribromopyrrole-3-carbonitrile in 20 mL of dry THF. After 15 minutes, 0.64 mL (10.3 mmol) of methyl iodide is added by syringe over 2 minutes. After several hours at room temperature, the mixture is diluted with 100 mL of water and 75 mL of ethyl acetate. The separated water phase is extracted again with ethyl acetate and the combined organic layers are washed with dilute sodium hydroxide, water, and saturated salt solution. After drying over magnesium sulfate, the mixture is shaken with activated charcoal and filtered. Concentration in vacuo gives a white solid which is slurried with hexane and recrystallized from ethyl acetate to afford the title compound as a white solid, mp 151°-152° C.

Workup

  1. waitAfter several hours at room temperature
  2. extractionThe separated water phase is extracted again with ethyl acetate
  3. washthe combined organic layers are washed with dilute sodium hydroxide, water, and saturated salt solution
  4. dry with materialAfter drying over magnesium sulfate
  5. filtrationfiltered
  6. concentrationConcentration in vacuo
  7. customgives a white solid which
  8. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-e6ad802535114896a55a49b3a75ea0d0
Source dataset
uspto-grants-1993_04
Patent number
US05204332

Reaction notes

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