Methyl iodide → HCID 22272847, compound

HRID 1064816Notes

Reaction equation

HRID 1064816 reaction equation
[H-].[Na+].[O:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[C:4]1[S:12][CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][N:18]([CH2:21][C:22]([NH:24][C:25]2[C:30]([CH:31]([CH3:33])[CH3:32])=[CH:29][C:28]([OH:34])=[CH:27][C:26]=2[CH:35]([CH3:37])[CH3:36])=[O:23])[CH2:17][CH2:16]1.I[CH3:39]>CN(C=O)C.O>[O:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[C:4]1[S:12][CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][N:18]([CH2:21][C:22]([NH:24][C:25]2[C:30]([CH:31]([CH3:32])[CH3:33])=[CH:29][C:28]([O:34][CH3:39])=[CH:27][C:26]=2[CH:35]([CH3:37])[CH3:36])=[O:23])[CH2:17][CH2:16]1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 22272702HCID 22272702, compound

Product 1

HCID 22272847HCID 22272847, compoundYield 43.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Sodium hydride (7 mg, 0.3 mmol) was added to a solution of 2-[4-[2-(benzoxazol-2-ylthio)ethyl]piperazin-1-yl]-N-(2,6-diisopropyl-4-hydroxyphenyl)acetamide (99 mg, 0.2 mmol) in DMF (2 ml), the mixture was heated at 60° C. for 10 minutes, and iodomethane (43 mg, 0.3 mmol) was dropped thereinto followed stirring for 30 minutes. The reaction solution was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and a saturated sodium chloride solution successively and dried over sodium sulfate and the solvent was evaporated therefrom. The residue was purified by a preparative thin layer chromatography (developing solvent, hexane:acetone 5:3) to provide 44 mg (yield 43%) of the desired compound as colorless needles.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materiala saturated sodium chloride solution successively and dried over sodium sulfate
  4. customthe solvent was evaporated
  5. customThe residue was purified by a preparative thin layer chromatography (developing solvent, hexane:acetone 5:3)

Sources & evidence

ORD record
ord-b0308fddb8ee49bf8808121ddca43e06
Source dataset
uspto-grants-2005_11
Patent number
US06969711B2

Reaction notes

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