Methyl iodide → HCID 13559601, compound

HRID 2309249Notes

Reaction equation

HRID 2309249 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([C:6]([NH:8][CH:9]([CH2:14][CH:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[NH:17][C:16]2=[O:24])[C:10]([O:12][CH3:13])=[O:11])=[O:7])=[CH:4][CH:3]=1.[C:27](=O)([O-])[O-].[Na+].[Na+].CI>CC(C)=O.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:8][CH:9]([CH2:14][C:15]2([CH3:27])[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[NH:17][C:16]2=[O:24])[C:10]([O:12][CH3:13])=[O:11])=[O:7])=[CH:25][CH:26]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 10340Sodium CarbonateHCID 13559600HCID 13559600, compound

Product 1

HCID 13559601HCID 13559601, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

2.4 Grams of methyl 2-(4-chlorobenzoylamino)-3-(oxindol-3-yl)propionate prepared in Example 57 was dissolved in 30 ml of acetone and 10 ml of water, then 0.34 g of sodium carbonate and 1 g of methyl iodide were added thereto and the reaction mixture was refluxed for 6 hours. Acetone was removed by evaporation, and the residue was extracted with chloroform, the chloroform layer was washed with water, dried with anhydrous magnesium sulfate, then the solvent was removed by evaporation. The residue was purified by means of a silica gel column chromatography (euting agent: chloroform/methanol=100/1) then recrystallized from hexane-ethyl acetate to obtain 0.5 g of methyl 2-(4-chlorobenzoylamino)-3-(3-methyloxindol-3-yl)propionate in the form of colorless needel-like crystals. Melting point: 201°-202° C.

Workup

  1. temperaturethe reaction mixture was refluxed for 6 hours
  2. customAcetone was removed by evaporation
  3. extractionthe residue was extracted with chloroform
  4. washthe chloroform layer was washed with water
  5. dry with materialdried with anhydrous magnesium sulfate
  6. customthe solvent was removed by evaporation
  7. customThe residue was purified by means of a silica gel column chromatography (euting agent: chloroform/methanol=100/1)
  8. customthen recrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-dce34ad3437442d58f1dfc8a1d99e0cb
Source dataset
uspto-grants-1987_09
Patent number
US04694017

Reaction notes

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