Thionyl Chloride → 4-(Chloromethyl)-1-ethyl-1H-pyrazole hydrochloride

HRID 2221661Notes

Reaction equation

HRID 2221661 reaction equation
[CH2:1]([N:3]1[CH:7]=[C:6]([CH2:8]O)[CH:5]=[N:4]1)[CH3:2].S(Cl)([Cl:12])=O>O1CCCC1>[ClH:12].[Cl:12][CH2:8][C:6]1[CH:5]=[N:4][N:3]([CH2:1][CH3:2])[CH:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 4711794(1-ethyl-1H-pyrazol-4-yl)methanol

Product 1

HCID 230765624-(Chloromethyl)-1-ethyl-1H-pyrazole hydrochlorideYield 100.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution (400 mL) of (1-ethyl-1H-pyrazol-4-yl)methanol (16.80 g) in tetrahydrofuran was added thionyl chloride (40.0 g), and the mixture was stirred at room temperature for 4 hr. The mixture liquid was concentrated under reduced pressure to obtain 4-chloromethyl-1-ethyl-1H-pyrazole hydrochloride as a colorless oil (24.15 g, yield 100%).

Workup

  1. concentrationThe mixture liquid was concentrated under reduced pressure

Sources & evidence

ORD record
ord-96222216876340cda1bf30403b692e93
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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