Methyl iodide → HCID 57579298, compound

HRID 732506Notes

Reaction equation

HRID 732506 reaction equation
S([O-])([O-])=O.[Na+].[Na+].[C:7](=O)(O)[O-].[Na+].[CH3:12][O:13][C:14](=[O:29])[C:15]1[CH:24]=[C:23]([S:25](Cl)(=[O:27])=[O:26])[CH:22]=[C:17]([C:18]([O:20][CH3:21])=[O:19])[CH:16]=1.IC>O.C(OCC)(=O)C.CN(C=O)C.C(O)C>[CH3:12][O:13][C:14](=[O:29])[C:15]1[CH:24]=[C:23]([S:25]([CH3:7])(=[O:27])=[O:26])[CH:22]=[C:17]([C:18]([O:20][CH3:21])=[O:19])[CH:16]=1

Participants

9

Reactant 4

HCID 6328Methyl iodideHCID 24437Sodium SulfiteHCID 516892Sodium BicarbonateHCID 37891971,3-Benzenedicarboxylic acid, 5-(chlorosulfonyl)-, 1,3-dimethyl ester

Product 1

HCID 57579298HCID 57579298, compound

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

Dissolve sodium sulfite (1.7 g, 13.51 mmol) and sodium bicarbonate (1.2 g, 14.19 mmol) in water (10 mL). Add 5-chlorosulfonyl-isophthalic acid dimethyl ester (2.0 g, 6.76 mmol) and ethanol (2 mL). Heat to 50° C. for 2 h, concentrate and dry the solid. Add DMF (40 mL) and iodomethane (4.56 g, 32 mmol) and stir at room temperature for 3 h. Dilute with ethyl acetate, wash with 10% aqueous potassium carbonate, 1 N lithium chloride and saturated aqueous sodium chloride. Dry (magnesium sulfate) and concentrate to give the title compound as a solid.

Workup

  1. concentrationconcentrate
  2. customdry the solid
  3. washwash with 10% aqueous potassium carbonate, 1 N lithium chloride and saturated aqueous sodium chloride
  4. dry with materialDry (magnesium sulfate)
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-9700cdfee45747f0b004f98ae2c893cc
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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