Thionyl Chloride → 2-[4-(Chloromethyl)-3-methyl-1H-pyrazol-1-YL]pyridine

HRID 349978

Reaction equation

HRID 349978 reaction equation
[CH3:1][C:2]1[C:6]([CH2:7]O)=[CH:5][N:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[N:3]=1.S(Cl)([Cl:17])=O>C1(C)C=CC=CC=1>[Cl:17][CH2:7][C:6]1[C:2]([CH3:1])=[N:3][N:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[CH:5]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 23076503[3-Methyl-1-(pyridin-2-yl)-1H-pyrazol-4-yl]methanol

Product 1

HCID 178612892-[4-(Chloromethyl)-3-methyl-1H-pyrazol-1-YL]pyridineYield 94%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 3-methyl-1-(2-pyridyl)-1H-pyrazol-4-ylmethanol (3.00 g), thionyl chloride (2.5 ml) and toluene (50 ml) was stirred at 70° C. for 2 hours. The reaction mixture was concentrated under reduced pressure, and saturated aqueous sodium bicarbonate solution was added to the residue, which was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4) and concentrated to obtain 4-chloromethyl-3-methyl-1-(2-pyridyl)-1H-pyrazole (3.10 g, yield 94%) as a colorless oily substance.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and saturated aqueous sodium bicarbonate solution
  2. additionwas added to the residue, which
  3. extractionwas extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6682ecdb3dad40cb984336166effd6f8
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Linked notes

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