Dimethylformamide → Methyl 4-[(4-chlorophenyl)sulfanyl]thiophene-3-carboxylate

HRID 1944419Notes

Reaction equation

HRID 1944419 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[C:10]([C:14]([OH:16])=[O:15])=[CH:11][S:12][CH:13]=2)=[CH:4][CH:3]=1.[C:17](=O)([O-])O.[Na+].IC.CN(C)C=O>O>[CH3:17][O:15][C:14]([C:10]1[C:9]([S:8][C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)=[CH:13][S:12][CH:11]=1)=[O:16]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 516892Sodium BicarbonateHCID 27789464-[(4-Chlorophenyl)sulfanyl]thiophene-3-carboxylic acid

Product 1

HCID 2778937Methyl 4-[(4-chlorophenyl)sulfanyl]thiophene-3-carboxylateYield 95.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-(4-chlorophenylsulfanyl)thiophene-3-carboxylic acid (1.0 g), sodium hydrogen carbonate (1.6 g), iodomethane (2.3 mL) and N,N-dimethylformamide (10 mL) was stirred was stirred at 40° C. for 5 hours. The mixture was cooled to room temperature, diluted with water (100 mL) and the aqueous phase extracted with ethyl acetate. The combined organic extract was dried over magnesium sulfate and concentrated under reduced pressure to afford the title compound as a yellow oil (1.0 g).

Workup

  1. stirringwas stirred at 40° C. for 5 hours
  2. extractionthe aqueous phase extracted with ethyl acetate
  3. extractionThe combined organic extract
  4. dry with materialwas dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8e29b40dcd244a228ebf2768ae96b247
Source dataset
uspto-grants-2013_03
Patent number
US08394836B2

Reaction notes

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