Dimethylformamide → HCID 58380609, compound

HRID 1802876Notes

Reaction equation

HRID 1802876 reaction equation
[CH3:1][S:2][C:3]1[NH:7][N:6]=[C:5]([CH:8]=[O:9])[CH:4]=1.[C:10](=O)([O-])[O-].[K+].[K+].CN(C=O)C.CI>O>[CH3:10][N:7]1[C:3]([S:2][CH3:1])=[CH:4][C:5]([CH:8]=[O:9])=[N:6]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178503272HCID 178503272, compound

Product 1

HCID 58380609HCID 58380609, compoundYield 58.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 5-(methylsulfanyl)-1H-pyrazole-3-carbaldehyde (10.0 g), potassium carbonate (9.70 g) and N,N′-dimethylformamide (60 mL) was slowly added methyl iodide (6.6 mL) at 0° C., and the mixture was stirred overnight at room temperature. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4), and concentrated. The obtained residue was subjected to silica gel column chromatography to give the title compound (6.38 g, yield 58%) as yellow crystals from the fraction eluted with ethyl acetate-hexane (1:5, volume ratio). melting point 47-48° C. MS: 157 (MH+).

Workup

  1. customat 0° C.
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with saturated brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-040f5130f30d4ff9b32b2150b4b3089a
Source dataset
uspto-grants-2013_01
Patent number
US08349886B2

Reaction notes

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