Dimethylformamide → 1-(3-chloro-2-pyridinyl)-5-methylthio-1H-pyrrole-2-carbaldehyde

HRID 252012Notes

Reaction equation

HRID 252012 reaction equation
[Cl:1][C:2]1[C:3]([N:8]2[C:12]([SH:13])=[CH:11][CH:10]=[C:9]2[CH:14]=[O:15])=[N:4][CH:5]=[CH:6][CH:7]=1.CI.[C:18](=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[Cl:1][C:2]1[C:3]([N:8]2[C:12]([S:13][CH3:18])=[CH:11][CH:10]=[C:9]2[CH:14]=[O:15])=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 866325651-(3-chloro-2-pyridinyl)-5-mercapto-1H-pyrrole-2-carbaldehyde

Product 1

HCID 866325661-(3-chloro-2-pyridinyl)-5-methylthio-1H-pyrrole-2-carbaldehydeYield 64.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.50 g of 1-(3-chloro-2-pyridinyl)-5-mercapto-1H-pyrrole-2-carbaldehyde, 0.36 g of methyl iodide, 0.43 g of potassium carbonate and 50 ml of N,N-dimethylformamide was stirred at room temperature for 1 day Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate three times. The organic layers were combined, washed successively with water and an aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.34 g of 1-(3-chloro-2-pyridinyl)-5-methylthio-1H-pyrrole-2-carbaldehyde of the formula:

Workup

  1. additionwas poured into the reaction mixture
  2. extractionthe mixture was extracted with ethyl acetate three times
  3. washwashed successively with water
  4. dry with materialan aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-52ac22b75a9f4ce58df6f37a640bdaec
Source dataset
uspto-grants-2011_01
Patent number
US07867949B2

Reaction notes

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