Sodium ethanethiolate → 4-[(ethylthio)methyl]-1-methyl-1H-pyrazole

HRID 339949Notes

Reaction equation

HRID 339949 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[N:5][N:6]([CH3:8])[CH:7]=1.[CH2:9]([S-:11])[CH3:10].[Na+]>CN(C)C=O>[CH2:9]([S:11][CH2:2][C:3]1[CH:4]=[N:5][N:6]([CH3:8])[CH:7]=1)[CH3:10]

Participants

4

Reactant 2

HCID 4459711Sodium ethanethiolateHCID 21698362HCID 21698362, compound2×

Product 1

HCID 119614244-[(ethylthio)methyl]-1-methyl-1H-pyrazoleYield 81.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-(chloromethyl)-1-methyl-1H-pyrazole (2.0 g, 15 mmol) (prepared according to Intermediate 5 Step A) and sodium ethanethiolate (2.6 g, 31 mmol) in N,N-dimethylformamide (20.0 mL) was stirred at room temperature overnight. The reaction mixture was quenched with brine and extracted with EtOAc (3×). The combined extracts were dried over Na2SO4, filtered and concentrated under reduced pressure to give an oil residue which was purified by combi-flash chromatography eluted with 20% EtOAc in hexane to give 1.9 g (79% yield) of the desired product. LC-MS found: 157.1 (M+H)+.

Workup

  1. customThe reaction mixture was quenched with brine
  2. extractionextracted with EtOAc (3×)
  3. dry with materialThe combined extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto give an oil residue which
  7. customwas purified by combi-flash chromatography
  8. washeluted with 20% EtOAc in hexane

Sources & evidence

ORD record
ord-ec82afde498a4cbf8996488165fc480a
Source dataset
uspto-grants-2014_11
Patent number
US08895571B2

Reaction notes

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