2,4,6-Trimethylpyridine → HCID 54270920, compound

HRID 1596042Notes

Reaction equation

HRID 1596042 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[CH:12]=[CH:13][CH2:14]O.N1C(C)=CC(C)=CC=1C.[Cl-].[Li+].CS([Cl:31])(=O)=O.[Cl-].[NH4+]>CN(C=O)C>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[CH:12]=[CH:13][CH2:14][Cl:31]

Participants

7

Reactant 5

HCID 79532,4,6-TrimethylpyridineHCID 25517Ammonium ChlorideHCID 31297Methanesulfonyl chlorideHCID 433294Lithium ChlorideHCID 53695575HCID 53695575, compound

Product 1

HCID 54270920HCID 54270920, compoundYield 38.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of Example 3C (0.85 g, 3.24 mmol), collidine (0.94 mL, 7.13 mmol) and lithium chloride (0.21 g, 4.97 mmol) in DMF (10 mL) at 0° C. was treated with methanesulfonyl chloride (0.38 mL, 4.87 mmol), stirred 16 hours at room temperature, poured into aqueous ammonium chloride, and extracted with ethyl acetate. The ethyl acetate was washed with water, brine, dried (MgSO4), filtered, concentrated, and purified on silica gel with 3% ethyl acetate/hexanes to provide 0.35 g (38%) of the desired compound.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate was washed with water, brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified on silica gel with 3% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-f86d65187ebf49978179d63f9dadab84
Source dataset
uspto-grants-2001_09
Patent number
US06288261B1

Reaction notes

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