Dimethylformamide → HCID 53584713, compound

HRID 2203011Notes

Reaction equation

HRID 2203011 reaction equation
[I:1][C:2]1[S:6][CH:5]=[C:4]([C:7]([OH:9])=[O:8])[CH:3]=1.IC.[C:12](=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[I:1][C:2]1[S:6][CH:5]=[C:4]([C:7]([O:9][CH3:12])=[O:8])[CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 470034485-Iodo-3-thiophenecarboxylic acid

Product 1

HCID 53584713HCID 53584713, compoundYield 98.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5-iodothiophene-3-carboxylic acid (3.48 g), iodomethane (2.92 g), potassium carbonate (2.84 g) and DMF (35 ml) was stirred at room temperature for 1 day. The reaction mixture was poured into water, and extracted with EtOAc. The extract was washed with brine, dried over MgSO4, concentrated and purified by silica gel column chromatography (hexane/EtOAc) to give the title compound (3.62 g) as a white solid.

Workup

  1. extractionextracted with EtOAc
  2. washThe extract was washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. custompurified by silica gel column chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-ccf7f8e582f54e4aa7d164c2a6422781
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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