Thionyl Chloride → 3-Chloromethyl-2-isopropylsulfanyl-pyridine

HRID 62832Notes

Reaction equation

HRID 62832 reaction equation
[CH:1]([S:4][C:5]1[C:10]([CH2:11]O)=[CH:9][CH:8]=[CH:7][N:6]=1)([CH3:3])[CH3:2].O=S(Cl)[Cl:15]>CC#N>[Cl:15][CH2:11][C:10]1[C:5]([S:4][CH:1]([CH3:3])[CH3:2])=[N:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 67085922HCID 67085922, compound

Product 1

HCID 538166813-Chloromethyl-2-isopropylsulfanyl-pyridineYield 92.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(2-Isopropylsulfanyl-pyridin-3-yl)-methanol (3.0 g, 16.37 mmol) obtained in Step B was dissolved in CH3CN (20 mL), and SOCl2(2.39 mL, 32.74 mmol) was added thereto dropwise at 0° C. The mixture was stirred at room temperature for 2 hours. After the termination of the reaction, the reactant was concentrated under reduced pressure. After the addition of EtOAc, the organic layer was washed with water, dried with MgSO4, filtrated and concentrated under reduced pressure to obtain the title compound (3.04 g, 92%).

Workup

  1. customdropwise at 0° C
  2. customAfter the termination of the reaction
  3. concentrationthe reactant was concentrated under reduced pressure
  4. additionAfter the addition of EtOAc
  5. washthe organic layer was washed with water
  6. dry with materialdried with MgSO4
  7. filtrationfiltrated
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-20995fbbfc6b478f815344b67e8bdfa3
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Reaction notes

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