Thionyl Chloride → 3-(chloromethyl)-1-ethyl-1H-pyrazole hydrochloride

HRID 79385Notes

Reaction equation

HRID 79385 reaction equation
[CH2:1]([N:3]1[CH:7]=[CH:6][C:5]([CH2:8]O)=[N:4]1)[CH3:2].S(Cl)([Cl:12])=O>C(Cl)Cl>[ClH:12].[Cl:12][CH2:8][C:5]1[CH:6]=[CH:7][N:3]([CH2:1][CH3:2])[N:4]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 22287713(1-ethyl-1H-pyrazol-3-yl)methanol

Product 1

HCID 672613403-(chloromethyl)-1-ethyl-1H-pyrazole hydrochlorideYield 91.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To (1-ethyl-1H-pyrazol-3-yl)methanol (4.41 g, 34.96 mmol) in DCM (30 mL) at 0° C. was cautiously added thionyl chloride (15.26 mL, 209.7 mmol). The cold bath was removed and the reaction mixture was stirred at ambient temperature for 3 hours. The mixture was concentrated under reduced pressure to give the crude product (5.78 g) which was used directly in the next step.

Workup

  1. customat 0° C.
  2. customThe cold bath was removed
  3. concentrationThe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-b779ad321b064b12ab3bbc32af4b7fe4
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Reaction notes

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