Methyl iodide → 2-(Methylsulfanylphenylamino-methylene)malonic acid diethyl ester

HRID 469933Notes

Reaction equation

HRID 469933 reaction equation
[CH3:1]I.[CH2:3]([O:5][C:6](=[O:22])[C:7](=[C:13]([SH:21])[NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH3:4].[Na]>CN(C=O)C>[CH2:11]([O:10][C:8](=[O:9])[C:7](=[C:13]([S:21][CH3:1])[NH:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[C:6]([O:5][CH2:3][CH3:4])=[O:22])[CH3:12]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 178472267HCID 178472267, compound

Product 1

HCID 155029782-(Methylsulfanylphenylamino-methylene)malonic acid diethyl esterYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Over a 30 min period, methyl iodide (17.7 g, 125 mmol) was added dropwise to a solution of sodium 2-(mercapto-phenylamino-methylene)-malonic acid diethyl ester (33 g, 104 mmol) in DMF (100 mL) cooled in an ice bath. The mixture was stirred at room temperature for 1 h, and then poured into ice water (300 mL). The resulting solid was collected via filtration, washed with water and dried to give 2-(methylsulfanyl-phenylamino-methylene)-malonic acid diethyl ester as a pale yellow solid (27 g, 84%).

Workup

  1. temperaturecooled in an ice bath
  2. filtrationThe resulting solid was collected via filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-71087587ff5842aab7c44f308da3dc72
Source dataset
uspto-grants-2014_01
Patent number
US08629162B2

Reaction notes

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