Methyl iodide → Methyl alpha-methylthio-alpha-(3-chloro-4-phthalimidophenyl)propionate

HRID 1733629Notes

Reaction equation

HRID 1733629 reaction equation
[CH3:1][S:2][CH:3]([C:8]1[CH:13]=[CH:12][C:11]([N:14]2[C:18](=[O:19])[C:17]3=[CH:20][CH:21]=[CH:22][CH:23]=[C:16]3[C:15]2=[O:24])=[C:10]([Cl:25])[CH:9]=1)[C:4]([O:6][CH3:7])=[O:5].[H-].[Na+].[CH3:28]I.[Cl-].[NH4+]>CN(C)C=O>[CH3:1][S:2][C:3]([C:8]1[CH:13]=[CH:12][C:11]([N:14]2[C:18](=[O:19])[C:17]3=[CH:20][CH:21]=[CH:22][CH:23]=[C:16]3[C:15]2=[O:24])=[C:10]([Cl:25])[CH:9]=1)([CH3:28])[C:4]([O:6][CH3:7])=[O:5]

Participants

6

Reactant 4

HCID 6328Methyl iodide2×HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 20556698HCID 20556698, compound

Product 1

HCID 12819454Methyl alpha-methylthio-alpha-(3-chloro-4-phthalimidophenyl)propionateYield 68%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl α-methylthio(3-chloro-4-phthalimidophenyl)acetate was dissolved in 4.0 ml of dimethylformamide, and with ice cooling and stirring, 82 mg (65% content) of sodium hydride was added. The mixture was stirred for 10 minutes. With ice cooling, 0.2 ml of methyl iodide was added, but the deep red color did not vanish. Hence, 0.2 ml of methyl iodide was further added, and the mixture was stirred for about 1.5 hours at room temperature. The color of the solution became lighter, and turned orange. To the reaction solution was added 20 ml of an aqueous solution of ammonium chloride, and the mixture was extracted twice with 10 ml of methylene chloride. The extract was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residual orange oil was chromatographed on a column of Florisil using methylene chloride as an eluent to afford 0.453 g (68%) of methyl α-methylthio-α-(3-chloro-4-phthalimidophenyl)propionate as colorless crystals.

Workup

  1. stirringThe mixture was stirred for 10 minutes
  2. stirringthe mixture was stirred for about 1.5 hours at room temperature
  3. extractionthe mixture was extracted twice with 10 ml of methylene chloride
  4. dry with materialThe extract was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residual orange oil was chromatographed on a column of Florisil

Sources & evidence

ORD record
ord-abfe5e21dec04a7fb39cad9a646bfe91
Source dataset
uspto-grants-1980_12
Patent number
US04242519

Reaction notes

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