Methyl iodide → HCID 22911377, compound

HRID 1378653Notes

Reaction equation

HRID 1378653 reaction equation
[CH3:1][N:2]([CH3:32])[C:3]1[N:7]([C:8]2[C:13]([Cl:14])=[CH:12][C:11]([Cl:15])=[CH:10][C:9]=2[Cl:16])[N:6]=[C:5]([S:17][CH3:18])[C:4]=1[CH2:19][N:20]1[CH:29]([CH2:30][OH:31])[CH2:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:21]1.[H-].[Na+].[CH3:35]I>O1CCCC1>[CH3:35][O:31][CH2:30][CH:29]1[CH2:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:21][N:20]1[CH2:19][C:4]1[C:5]([S:17][CH3:18])=[N:6][N:7]([C:8]2[C:9]([Cl:16])=[CH:10][C:11]([Cl:15])=[CH:12][C:13]=2[Cl:14])[C:3]=1[N:2]([CH3:1])[CH3:32]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 67690226HCID 67690226, compound

Product 1

HCID 22911377HCID 22911377, compoundYield 57.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the racemic mixture of Example 7 (200 mg, 0.39 mmol) in anhydrous tetrahydrofuran (2.0 ml), sodium hydride (78 mg of 60% sodium hydride mineral oil dispersion; 46 mg, 2.0 mmol of sodium hydride) was added; and the resulting mixture was stirred for 15 minutes at ambient temperature. Methyl iodide (0.10 ml, 1.6 mmol) was added, and the mixture was stirred for 18 hours at ambient temperature. The solvent was removed in vacuo, and the residue was dissolved in ethyl acetate/water (20 ml of each). The aqueous phase was separated and extracted with three equal volumes of ethyl acetate. The combined organic extracts were dried (anhydrous sodium sulfate) and concentrated in vacuo to a yellow oil. Flash chromatography of the entire sample (silica gel, 40 micron mesh; elution with ethyl acetate/hexane=1:10 in volume) afforded the title compound (118 mg) as a light-yellow oil.

Workup

  1. stirringthe mixture was stirred for 18 hours at ambient temperature
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue was dissolved in ethyl acetate/water (20 ml of each)
  4. customThe aqueous phase was separated
  5. extractionextracted with three equal volumes of ethyl acetate
  6. dry with materialThe combined organic extracts were dried (anhydrous sodium sulfate)
  7. concentrationconcentrated in vacuo to a yellow oil
  8. washFlash chromatography of the entire sample (silica gel, 40 micron mesh; elution with ethyl acetate/hexane=1:10 in volume)

Sources & evidence

ORD record
ord-5a0e45f603e44099bd6215a7342bf532
Source dataset
uspto-grants-1997_09
Patent number
US05668145

Reaction notes

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